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(1)]. They are formed by the covalent addition... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14588171" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">Anionic s complexes, also referred to as "Jackson-Meisenheimer" or "Meisenheimer" complexes, are key intermediates in the S N Ar mechanism of aromatic nucleophilic substitution reactions [Eq. (1)]. They are formed by the covalent addition of nucleophiles (Nu À ) to aromatic substrates bearing electron-withdrawing substituents (X) and have been characterized as stable or transient species by X-ray crystallography, NMR, and UV/Vis spectroscopy in condensed phases. As compared with the wealth of kinetic and thermodynamic studies on Meisenheimer complexes in solution, relatively few studies are concerned with their gas-phase chemistry. [3] In a recent report, the exceedingly fast reaction of fluoride ion with nitrobenzene was ascribed to a potentialenergy profile where the anionic ipso complex is a transition state rather than a stable species lying in a local energy minimum. A transition towards an energy profile displaying an anionic s complex intermediate is predicted by DFT calculations, as the para position with respect to the NO 2 leaving group (Y = NO 2 ) is substituted by an electron-withdrawing group. Gas-phase thermochemical data for the equilibria involving the addition of anions to substituted benzenes have been obtained by high-pressure mass spec-trometry, thereby providing information on the stabilities of the complexes though not directly on their structures. [6] Indeed, depending on the nature of the substituents on the benzene ring and the nature of Nu À , various stable structures can occur and structural assignments have relied largely on calculations. [6][7] The structural elucidation of prototypical Meisenheimer complexes in the gas phase is reported herein. To this end, a spectroscopic methodology is applied that is based on the coupling of the radiation output of an IR free-electron laser (FEL) at the CLIO (Centre Laser Infrarouge dOrsay) European facility with a Paul-type ion-trap mass spectrometer, thus exploiting the potential emerging from the combination of mass spectrometry with an IR FEL radiation source. [9] The IR features of a gaseous ion may be disclosed in the IR multiphoton dissociation (IRMPD) spectrum, which reports the resonance-enhanced photofragmentation process following multiple-photon absorption in correspondence with the IR active modes of the sampled species. Among the several recent achievements, IRMPD spectra have been reported for few inorganic negative ions, including complexes of halide ions, iron carbonyl clusters, and vanadium oxide cluster anions. When a basic methanol solution of 1,3,5-trinitrobenzene (TNB) is subjected to electrospray ionization (ESI) in the negative-ion mode, the adduct ion incorporating the anion of the solvent, [CH 3 OC 6 H 3 (NO 2 ) 3 ] À , is the major ionic species observed. The structural assay of the so-formed species is gained by IRMPD spectroscopy, whereby the ion is isolated in the ion trap and allowed to interact with the IR FEL radiation. A wavelength-dependent dissociation process leads to a major product ion formally corresponding to deprotonated TNB [Eq. (2 a)], implying loss of a methanol molecule. These products are thermodynamically favored with respect to the alkoxide ion and neutral TNB pair, owing to the higher acidity of nitrobenzene relative to primary alcohols. A second, minor dissociation pathway [Eq. (2 b)] occurs by formal loss of neutral methyl nitrite, leading to 2,4dinitrophenoxide as the likely product ion in a process involving substantial bonding rearrangement.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14588171" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="6a4185d1fc1d6130a67caf7643ef966c" rel="nofollow" data-download="{"attachment_id":44052045,"asset_id":14588171,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44052045/download_file?st=MTc0MTMxNzg4OSw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33542922" href="https://independent.academia.edu/PhilippeMa%C3%AEtre">Philippe Maître</a><script data-card-contents-for-user="33542922" type="text/json">{"id":33542922,"first_name":"Philippe","last_name":"Maître","domain_name":"independent","page_name":"PhilippeMaître","display_name":"Philippe Maître","profile_url":"https://independent.academia.edu/PhilippeMa%C3%AEtre","photo":"/images/s65_no_pic.png"}</script></span></span><span class="u-displayInlineBlock InlineList-item-text"> and <span class="u-textDecorationUnderline u-clickable InlineList-item-text js-work-more-authors-14588171">+1</span><div class="hidden js-additional-users-14588171"><div><span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a></span></div></div></span><script>(function(){ var popoverSettings = { el: $('.js-work-more-authors-14588171'), placement: 'bottom', hide_delay: 200, html: true, content: function(){ return $('.js-additional-users-14588171').html(); 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(1)]. They are formed by the covalent addition of nucleophiles (Nu À ) to aromatic substrates bearing electron-withdrawing substituents (X) and have been characterized as stable or transient species by X-ray crystallography, NMR, and UV/Vis spectroscopy in condensed phases. As compared with the wealth of kinetic and thermodynamic studies on Meisenheimer complexes in solution, relatively few studies are concerned with their gas-phase chemistry. [3] In a recent report, the exceedingly fast reaction of fluoride ion with nitrobenzene was ascribed to a potentialenergy profile where the anionic ipso complex is a transition state rather than a stable species lying in a local energy minimum. A transition towards an energy profile displaying an anionic s complex intermediate is predicted by DFT calculations, as the para position with respect to the NO 2 leaving group (Y = NO 2 ) is substituted by an electron-withdrawing group. Gas-phase thermochemical data for the equilibria involving the addition of anions to substituted benzenes have been obtained by high-pressure mass spec-trometry, thereby providing information on the stabilities of the complexes though not directly on their structures. [6] Indeed, depending on the nature of the substituents on the benzene ring and the nature of Nu À , various stable structures can occur and structural assignments have relied largely on calculations. [6][7] The structural elucidation of prototypical Meisenheimer complexes in the gas phase is reported herein. To this end, a spectroscopic methodology is applied that is based on the coupling of the radiation output of an IR free-electron laser (FEL) at the CLIO (Centre Laser Infrarouge dOrsay) European facility with a Paul-type ion-trap mass spectrometer, thus exploiting the potential emerging from the combination of mass spectrometry with an IR FEL radiation source. [9] The IR features of a gaseous ion may be disclosed in the IR multiphoton dissociation (IRMPD) spectrum, which reports the resonance-enhanced photofragmentation process following multiple-photon absorption in correspondence with the IR active modes of the sampled species. Among the several recent achievements, IRMPD spectra have been reported for few inorganic negative ions, including complexes of halide ions, iron carbonyl clusters, and vanadium oxide cluster anions. When a basic methanol solution of 1,3,5-trinitrobenzene (TNB) is subjected to electrospray ionization (ESI) in the negative-ion mode, the adduct ion incorporating the anion of the solvent, [CH 3 OC 6 H 3 (NO 2 ) 3 ] À , is the major ionic species observed. The structural assay of the so-formed species is gained by IRMPD spectroscopy, whereby the ion is isolated in the ion trap and allowed to interact with the IR FEL radiation. A wavelength-dependent dissociation process leads to a major product ion formally corresponding to deprotonated TNB [Eq. (2 a)], implying loss of a methanol molecule. These products are thermodynamically favored with respect to the alkoxide ion and neutral TNB pair, owing to the higher acidity of nitrobenzene relative to primary alcohols. A second, minor dissociation pathway [Eq. (2 b)] occurs by formal loss of neutral methyl nitrite, leading to 2,4dinitrophenoxide as the likely product ion in a process involving substantial bonding rearrangement.","publication":"Angewandte Chemie International Edition","publication_with_fallback":"Angewandte Chemie International 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Maître","profile_url":"https://independent.academia.edu/PhilippeMa%C3%AEtre","photo":"/images/s65_no_pic.png"},{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}],"research_interests":[{"id":3614,"name":"Structure","url":"https://www.academia.edu/Documents/in/Structure","nofollow":true},{"id":11074,"name":"Aromatic Molecules","url":"https://www.academia.edu/Documents/in/Aromatic_Molecules","nofollow":true},{"id":178071,"name":"IR and UV spectroscopy of gas phase molecules and molecular ions","url":"https://www.academia.edu/Documents/in/IR_and_UV_spectroscopy_of_gas_phase_molecules_and_molecular_ions","nofollow":true},{"id":260118,"name":"CHEMICAL 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u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14588192 coauthored" data-work_id="14588192" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14588192/S_nitrosation_of_cysteine_as_evidenced_by_IRMPD_spectroscopy">S-nitrosation of cysteine as evidenced by IRMPD spectroscopy</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">Density functional calculations 22 a b s t r a c t S-nitrosation of cysteine plays an important role in storage and transport of NO, a key signaling molecule in vivo. An approach to detect this modification in the bare, charged amino acid... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14588192" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">Density functional calculations 22 a b s t r a c t S-nitrosation of cysteine plays an important role in storage and transport of NO, a key signaling molecule in vivo. An approach to detect this modification in the bare, charged amino acid is presented, based on IR multiple photon dissociation (IRMPD) spectroscopy. Protonated and deprotonated S-nitrosocysteine ions, [SNOCys+H] + and [SNOCys−H] − , have been obtained by electrospray ionization and assayed for IR activity in either the 1000-1900 cm −1 or the 3000-3600 cm −1 wavenumber range. The so-obtained IRMPD spectra display characteristic features ascribed to the presence of the S-nitrosation motif, which are missing in the corresponding IRMPD spectra of the native cysteine ions, [Cys+H] + and [Cys−H] − . In particular, the NO stretching mode is unambiguously identified by the red shift observed for the 15 N-labelled species. The interpretation of the IRMPD spectra is supported by density functional theory calculations of the optimized geometries, relative energies and IR spectra of [SNOCys+H] + and [SNO-Cys−H] − . Both sampled ions comprise a thermally averaged population of conformers contributing to the experimental IRMPD spectra. This notion is supported by the agreement between the convoluted IR spectra of the several conformers, and the recorded IRMPD spectrum. The gathered evidence points to a characteristic NO stretching mode that emerges as a pronounced feature at 1460-1490 cm −1 in the IRMPD spectrum of [SNOCys−H] − , namely in a region where [Cys−H] − displays no IRMPD activity. Conversely, the NO stretching vibration of [SNOCys+H] + is enclosed in a wide absorption including the C O stretching mode at 1780 cm −1 . The [SNOCys−H] − negative ions are thus a promising benchmark in a search for S-nitrosation features using IRMPD spectroscopy. contribution infra-red multiple photon dissociation (IRMPD) spec-35 troscopy, based on the use of an IR radiation source of high 36 power and wide tunability combined with tandem mass spectrom-37 etry, has been exploited to gain insight into the structural and 38 spectroscopic features of ions derived from SNOCys. The ions deliv-39 ered into the gas phase by electrospray ionization are either the 40 protonated molecule, [SNOCys+H] + , or the deprotonated species 41 [SNOCysNO−H] − . The high degree of in-depth information that can 42 be gained by IRMPD spectroscopy of the ionic species obtained 43 from the natural amino acids is well illustrated in several recent 44 papers and review articles [10-27]. In particular, a notable effort 45 has been devoted to ascertain the conditions favoring zwitterionic 46 structures and to unambiguously characterize them. The sample 47 ions obtained by protonation or deprotonation of native cysteine 48 ([Cys+H] + and [Cys−H] − , respectively) have been already assayed 49 by IRMPD spectroscopy in the 600-1800 cm −1 IR range and the 50 experimental spectra have been discussed in association with the 51 calculated IR spectra of the most stable conformers in two landmark 52 papers [28,29]. The deprotonated cysteine ion has been probed as 53 model ion in view of the current interest about the structure of 54 ions formed by electrospray ionization (ESI) [30-33]. Whether they 55 G Model MASPEC 14739 1-7 2 F. Lanucara et al. / International Journal of Mass Spectrometry xxx (2012) xxx-xxx retain their former structure in solution or rather adopt the one 56 thermodynamically favored in the gas phase is a topic of active 57 investigation and debate. The deprotonated cysteine ion displays 58 an experimental IRMPD spectrum consistent with a carboxylate 59 structure (deprotonation on the COOH group) although the thio-60 late structure (deprotonation on the SH group) is calculated to be 61 lower in energy [30,34,35]. 62 [Cys+H] + and [Cys−H] − ions are now re-examined as refer-63 ence species to aid in identifying distinctive signatures for the 64 nitrosation feature in the IRMPD spectra of [SNOCys+H] + and [SNO-65 Cys−H] − . 66 2. Experimental details 67 2.1. Materials 68 l-Cysteine hydrochloride, NaNO 2 , Na 15 NO 2 and all the solvents 69 used in this work were research grade products from commercial 70 sources (Sigma-Aldrich s.r.l. Milan, Italy) and were used without 71 any further purification. S-nitrosocysteine was obtained from the 72 reaction of l-cysteine (2 mM) and NaNO 2 or Na 15 NO 2 (2 mM) in 73 H 2 O:CH 3 CN 1:1 (2 ml) at 37 • C, by adding H 2 SO 4 (98%) to the reac-74 tion mixture to pH 1.5, followed by a 1 in 100 dilution in H 2 O:CH 3 CN 75 1:1. An alternative method has also been assayed, allowing l-76 cysteine (20 mM in H 2 O:CH 3 CN) to react with NO (1 bar) after 77 purging the solution and the flask repeatedly with Ar. UV-vis spec-78 troscopy has been used to confirm the formation and stability of 79 S-nitrosocysteine by monitoring the presence of the band at 543 nm 80 assigned to an n → * charge-transfer transition. Soon after prepa-81 ration of the compound (which occurs on mixing), diluted solutions 82 (about 7 M) for ESI-MS experiments were prepared. ESI-MS anal-83 ysis shows the protonated molecule [SNOCys+H] + at m/z 151, the 84 protonated disulfide (protonated cystine) at m/z 241 and the cys-85 teine radical cation at m/z 121. The deprotonated amino acids are 86 generated by ESI of 0.1 mM solutions in H 2 O:CH 3 CN 1:1 by the 87 addition of NH 3 to assist deprotonation. 88 2.2. IRMPD experiments 89 IRMPD experiments on the protonated and deprotonated forms 90 of S-nitrosocysteine and cysteine have been performed in two spec-91 tral regions, namely 1000-2000 cm −1 and 3200-3600 cm −1 , using 92 two different IR radiation sources, the free electron laser (FEL) at 93 the Centre Laser Infrarouge d'Orsay (CLIO) facility and an Opti-94 cal Parametric Oscillator/Amplifier (OPO/OPA) laser system at the 95 Università di Roma "La Sapienza", respectively. The FEL radiation 96 G Model MASPEC 14739 1-7 F. Lanucara et al. / International Journal of Mass Spectrometry xxx (2012) xxx-xxx 7 significant IRMPD activity in a relatively wide region between 1313 438 and 1647 cm −1 , namely the frequency positions of the symmet-439 ric and asymmetric −CO 2 − stretching modes. It is in this blank 440 interval that [SNOCys−H] − ions display a remarkable, 15 N-isotope-441 sensitive band. The band is assigned to the NO stretching vibration 442 and stands out as a notable signature for S-nitrosation. A similar, 443 clearcut piece of information cannot be gained from IRMPD spec-444 troscopy of the positively charged [SNOCys+H] + ion. For this species 445 the informative NO stretching mode is active at a frequency close to 446 the C O stretching resonance, yielding a broad, unresolved absorp-447 tion. Indeed, a (partial) separation of the two modes is revealed 448 only in the spectrum of the 15 N-labelled [S 15 NOCys+H] + ion, which 449 allowed to identify the distinct presence and activity of the two 450 modes. 451 The unambiguous identification of the nitrosation feature in 452 the IRMPD spectrum of deprotonated S-nitrosocysteine provides 453 a characteristic signature of this modification. In a similar way, 454 characteristic IRMPD signatures have been identified for the phos-455 phorylation of amino acids and peptides [60-62], for the nitration 456 of tyrosine [38] and for the sulfide to sulfoxide oxidation in methi-457 onine and related compounds [63]. 458 Acknowledgements 459 Financial support was provided by the Italian Ministero 460 dell'Istruzione, dell'Università e della Ricerca and by the European 461 Community's Seventh Framework Programme (FP7/2007-2013, 462 under grant agreement no. 226716) which provided also travel 463 funding to F.L., M.E.C. and B.C. for access to the European multi-user 464 facility CLIO. The skilful assistance of the CLIO team under the direc-465 tion of J.M. Ortega and of Joel Lemaire, in charge of the beamline, is 466 gratefully acknowledged. 467 Appendix A. Supplementary data 468 Supplementary data associated with this article can be found, in 469 the online version, at http://dx.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14588192" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="a56a32af0ef86364de266bfab029ce1c" rel="nofollow" data-download="{"attachment_id":44052043,"asset_id":14588192,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44052043/download_file?st=MTc0MTMxNzg4OSw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33542922" href="https://independent.academia.edu/PhilippeMa%C3%AEtre">Philippe Maître</a><script data-card-contents-for-user="33542922" type="text/json">{"id":33542922,"first_name":"Philippe","last_name":"Maître","domain_name":"independent","page_name":"PhilippeMaître","display_name":"Philippe Maître","profile_url":"https://independent.academia.edu/PhilippeMa%C3%AEtre","photo":"/images/s65_no_pic.png"}</script></span></span><span class="u-displayInlineBlock InlineList-item-text"> and <span class="u-textDecorationUnderline u-clickable InlineList-item-text js-work-more-authors-14588192">+1</span><div class="hidden js-additional-users-14588192"><div><span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a></span></div></div></span><script>(function(){ var popoverSettings = { el: $('.js-work-more-authors-14588192'), placement: 'bottom', hide_delay: 200, html: true, content: function(){ return $('.js-additional-users-14588192').html(); 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An approach to detect this modification in the bare, charged amino acid is presented, based on IR multiple photon dissociation (IRMPD) spectroscopy. Protonated and deprotonated S-nitrosocysteine ions, [SNOCys+H] + and [SNOCys−H] − , have been obtained by electrospray ionization and assayed for IR activity in either the 1000-1900 cm −1 or the 3000-3600 cm −1 wavenumber range. The so-obtained IRMPD spectra display characteristic features ascribed to the presence of the S-nitrosation motif, which are missing in the corresponding IRMPD spectra of the native cysteine ions, [Cys+H] + and [Cys−H] − . In particular, the NO stretching mode is unambiguously identified by the red shift observed for the 15 N-labelled species. The interpretation of the IRMPD spectra is supported by density functional theory calculations of the optimized geometries, relative energies and IR spectra of [SNOCys+H] + and [SNO-Cys−H] − . Both sampled ions comprise a thermally averaged population of conformers contributing to the experimental IRMPD spectra. This notion is supported by the agreement between the convoluted IR spectra of the several conformers, and the recorded IRMPD spectrum. The gathered evidence points to a characteristic NO stretching mode that emerges as a pronounced feature at 1460-1490 cm −1 in the IRMPD spectrum of [SNOCys−H] − , namely in a region where [Cys−H] − displays no IRMPD activity. Conversely, the NO stretching vibration of [SNOCys+H] + is enclosed in a wide absorption including the C O stretching mode at 1780 cm −1 . The [SNOCys−H] − negative ions are thus a promising benchmark in a search for S-nitrosation features using IRMPD spectroscopy. contribution infra-red multiple photon dissociation (IRMPD) spec-35 troscopy, based on the use of an IR radiation source of high 36 power and wide tunability combined with tandem mass spectrom-37 etry, has been exploited to gain insight into the structural and 38 spectroscopic features of ions derived from SNOCys. The ions deliv-39 ered into the gas phase by electrospray ionization are either the 40 protonated molecule, [SNOCys+H] + , or the deprotonated species 41 [SNOCysNO−H] − . The high degree of in-depth information that can 42 be gained by IRMPD spectroscopy of the ionic species obtained 43 from the natural amino acids is well illustrated in several recent 44 papers and review articles [10-27]. In particular, a notable effort 45 has been devoted to ascertain the conditions favoring zwitterionic 46 structures and to unambiguously characterize them. The sample 47 ions obtained by protonation or deprotonation of native cysteine 48 ([Cys+H] + and [Cys−H] − , respectively) have been already assayed 49 by IRMPD spectroscopy in the 600-1800 cm −1 IR range and the 50 experimental spectra have been discussed in association with the 51 calculated IR spectra of the most stable conformers in two landmark 52 papers [28,29]. The deprotonated cysteine ion has been probed as 53 model ion in view of the current interest about the structure of 54 ions formed by electrospray ionization (ESI) [30-33]. Whether they 55 G Model MASPEC 14739 1-7 2 F. Lanucara et al. / International Journal of Mass Spectrometry xxx (2012) xxx-xxx retain their former structure in solution or rather adopt the one 56 thermodynamically favored in the gas phase is a topic of active 57 investigation and debate. The deprotonated cysteine ion displays 58 an experimental IRMPD spectrum consistent with a carboxylate 59 structure (deprotonation on the COOH group) although the thio-60 late structure (deprotonation on the SH group) is calculated to be 61 lower in energy [30,34,35]. 62 [Cys+H] + and [Cys−H] − ions are now re-examined as refer-63 ence species to aid in identifying distinctive signatures for the 64 nitrosation feature in the IRMPD spectra of [SNOCys+H] + and [SNO-65 Cys−H] − . 66 2. Experimental details 67 2.1. Materials 68 l-Cysteine hydrochloride, NaNO 2 , Na 15 NO 2 and all the solvents 69 used in this work were research grade products from commercial 70 sources (Sigma-Aldrich s.r.l. Milan, Italy) and were used without 71 any further purification. S-nitrosocysteine was obtained from the 72 reaction of l-cysteine (2 mM) and NaNO 2 or Na 15 NO 2 (2 mM) in 73 H 2 O:CH 3 CN 1:1 (2 ml) at 37 • C, by adding H 2 SO 4 (98%) to the reac-74 tion mixture to pH 1.5, followed by a 1 in 100 dilution in H 2 O:CH 3 CN 75 1:1. An alternative method has also been assayed, allowing l-76 cysteine (20 mM in H 2 O:CH 3 CN) to react with NO (1 bar) after 77 purging the solution and the flask repeatedly with Ar. UV-vis spec-78 troscopy has been used to confirm the formation and stability of 79 S-nitrosocysteine by monitoring the presence of the band at 543 nm 80 assigned to an n → * charge-transfer transition. Soon after prepa-81 ration of the compound (which occurs on mixing), diluted solutions 82 (about 7 M) for ESI-MS experiments were prepared. ESI-MS anal-83 ysis shows the protonated molecule [SNOCys+H] + at m/z 151, the 84 protonated disulfide (protonated cystine) at m/z 241 and the cys-85 teine radical cation at m/z 121. The deprotonated amino acids are 86 generated by ESI of 0.1 mM solutions in H 2 O:CH 3 CN 1:1 by the 87 addition of NH 3 to assist deprotonation. 88 2.2. IRMPD experiments 89 IRMPD experiments on the protonated and deprotonated forms 90 of S-nitrosocysteine and cysteine have been performed in two spec-91 tral regions, namely 1000-2000 cm −1 and 3200-3600 cm −1 , using 92 two different IR radiation sources, the free electron laser (FEL) at 93 the Centre Laser Infrarouge d'Orsay (CLIO) facility and an Opti-94 cal Parametric Oscillator/Amplifier (OPO/OPA) laser system at the 95 Università di Roma \"La Sapienza\", respectively. The FEL radiation 96 G Model MASPEC 14739 1-7 F. Lanucara et al. / International Journal of Mass Spectrometry xxx (2012) xxx-xxx 7 significant IRMPD activity in a relatively wide region between 1313 438 and 1647 cm −1 , namely the frequency positions of the symmet-439 ric and asymmetric −CO 2 − stretching modes. It is in this blank 440 interval that [SNOCys−H] − ions display a remarkable, 15 N-isotope-441 sensitive band. The band is assigned to the NO stretching vibration 442 and stands out as a notable signature for S-nitrosation. A similar, 443 clearcut piece of information cannot be gained from IRMPD spec-444 troscopy of the positively charged [SNOCys+H] + ion. For this species 445 the informative NO stretching mode is active at a frequency close to 446 the C O stretching resonance, yielding a broad, unresolved absorp-447 tion. Indeed, a (partial) separation of the two modes is revealed 448 only in the spectrum of the 15 N-labelled [S 15 NOCys+H] + ion, which 449 allowed to identify the distinct presence and activity of the two 450 modes. 451 The unambiguous identification of the nitrosation feature in 452 the IRMPD spectrum of deprotonated S-nitrosocysteine provides 453 a characteristic signature of this modification. In a similar way, 454 characteristic IRMPD signatures have been identified for the phos-455 phorylation of amino acids and peptides [60-62], for the nitration 456 of tyrosine [38] and for the sulfide to sulfoxide oxidation in methi-457 onine and related compounds [63]. 458 Acknowledgements 459 Financial support was provided by the Italian Ministero 460 dell'Istruzione, dell'Università e della Ricerca and by the European 461 Community's Seventh Framework Programme (FP7/2007-2013, 462 under grant agreement no. 226716) which provided also travel 463 funding to F.L., M.E.C. and B.C. for access to the European multi-user 464 facility CLIO. The skilful assistance of the CLIO team under the direc-465 tion of J.M. Ortega and of Joel Lemaire, in charge of the beamline, is 466 gratefully acknowledged. 467 Appendix A. Supplementary data 468 Supplementary data associated with this article can be found, in 469 the online version, at http://dx.","publication":"International Journal of Mass Spectrometry","publication_with_fallback":"International Journal of Mass 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js-work-card work_14588249 coauthored" data-work_id="14588249" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14588249/IR_Spectroscopic_Features_of_Gaseous_C7H7O_Ions_Benzylium_versus_Tropylium_Ion_Structures">IR Spectroscopic Features of Gaseous C7H7O+ Ions: Benzylium versus Tropylium Ion Structures</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">Gaseous [C 7 H 7 O] + ions have been formed by protonation of benzaldehyde or tropone (2,4,6-cycloheptatrienone) in the cell of an FT-ICR mass spectrometer using C 2 H 5 + as a Brønsted acid. The so-formed species have been assayed by... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14588249" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">Gaseous [C 7 H 7 O] + ions have been formed by protonation of benzaldehyde or tropone (2,4,6-cycloheptatrienone) in the cell of an FT-ICR mass spectrometer using C 2 H 5 + as a Brønsted acid. The so-formed species have been assayed by infrared multiphoton dissociation (IRMPD) using the free electron laser (FEL) at the CLIO (Centre Laser Infrarouge Orsay) facility. The IRMPD features are quite distinct for ions from the two different precursors, pointing to two different isomers. A number of potential structures for [C 7 H 7 O] + ions have been optimized at the B3LYP/6-31+G(d,p) level of theory, and their relative energies and IR spectra are reported. On this basis, the IRMPD spectra of [C 7 H 7 O] + ions are found to display features characteristic of O-protonated species, with no evidence of any further skeletal rearrangements. The so-formed ions are thus hydroxysubstituted benzylium and tropylium ions, respectively, representative members of the benzylium/tropylium ion family. The IRMPD assay using the FEL laser light has allowed their unambiguous discrimination where other mass spectrometric techniques have yielded a less conclusive answer.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14588249" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="f29401182d7dcad448f14a94e71844da" rel="nofollow" data-download="{"attachment_id":44051709,"asset_id":14588249,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44051709/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33542922" href="https://independent.academia.edu/PhilippeMa%C3%AEtre">Philippe Maître</a><script data-card-contents-for-user="33542922" type="text/json">{"id":33542922,"first_name":"Philippe","last_name":"Maître","domain_name":"independent","page_name":"PhilippeMaître","display_name":"Philippe Maître","profile_url":"https://independent.academia.edu/PhilippeMa%C3%AEtre","photo":"/images/s65_no_pic.png"}</script></span></span><span class="u-displayInlineBlock InlineList-item-text"> and <span class="u-textDecorationUnderline u-clickable InlineList-item-text js-work-more-authors-14588249">+1</span><div class="hidden js-additional-users-14588249"><div><span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a></span></div></div></span><script>(function(){ var popoverSettings = { el: $('.js-work-more-authors-14588249'), placement: 'bottom', hide_delay: 200, html: true, content: function(){ return $('.js-additional-users-14588249').html(); 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The so-formed species have been assayed by infrared multiphoton dissociation (IRMPD) using the free electron laser (FEL) at the CLIO (Centre Laser Infrarouge Orsay) facility. The IRMPD features are quite distinct for ions from the two different precursors, pointing to two different isomers. A number of potential structures for [C 7 H 7 O] + ions have been optimized at the B3LYP/6-31+G(d,p) level of theory, and their relative energies and IR spectra are reported. On this basis, the IRMPD spectra of [C 7 H 7 O] + ions are found to display features characteristic of O-protonated species, with no evidence of any further skeletal rearrangements. The so-formed ions are thus hydroxysubstituted benzylium and tropylium ions, respectively, representative members of the benzylium/tropylium ion family. The IRMPD assay using the FEL laser light has allowed their unambiguous discrimination where other mass spectrometric techniques have yielded a less conclusive answer.","publication":null,"publication_with_fallback":null,"downloadable_attachments":[{"id":44051709,"asset_id":14588249,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44051709/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44051709/jp0628380-libre.pdf20160323-25187-1t2u194?1458789502=\u0026response-content-disposition=attachment%3B+filename%3DIR_Spectroscopic_Features_of_Gaseous_C7H.pdf\u0026Expires=1741321489\u0026Signature=SSj11JIxT1lXYR~0b9KX7IFDCVsUYfzwSlyAdp4Z9-JSijjJRZP8nywxWoKRaRRH6j0vaXPDsXk1~0LvhB6Yx-4uYZfXRYzBD0KK6rfa-naWOhrrbpuIdkA1hSNOBNfqZBUp78gBF0PMN8hmc0Sl79HJN4CE0xP9xksp5BVpIoRvYcqbrprxGnY43-1736gBvsRMoctqKyrja75iy1HzqGPfvRrodx2yzq~Je0ZOc8zn1THAWiml4YWj32Xw-jbThkxINl1cGgEUyL~eIVG8Epp-fQ3KJg6TY9ccLQFzD5E596Pn82DDcJutOd5WwRaQkZvhljK720lgSCICCJhJWw__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44051709/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44051709/mini_magick20220711-1586-17v6hem.png?1657603043"}],"downloadable_attachments_with_full_thumbnails":[{"id":44051709,"asset_id":14588249,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44051709/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44051709/jp0628380-libre.pdf20160323-25187-1t2u194?1458789502=\u0026response-content-disposition=attachment%3B+filename%3DIR_Spectroscopic_Features_of_Gaseous_C7H.pdf\u0026Expires=1741321490\u0026Signature=gKVTUY-OJDGvQ9iQmcOnfaqYm~7x0--dS05TZ3j8RvVMZhD8tgrTKHkpjezeBz75UWepV4dLpodaJmz8qsLAn-pghXFJsBQ0NSmrzbzDif0pZ-6h21hzHKHn7JnlurhJ035XNRMbFNBrjFe9gYl1Z4qwm3SNd0LgvpHXQePzxHvCImUyIKSHr236ZHT6ltL5j5UvpYQN0nxifUwkRa1bY2XHehdVFYcHfqHQ8gWsJThg6HD5lEfByLeIvEBwI4zt73CRPxFuNBP2~wo43o-1-BbYUUwVPn9X0WwdgejcL6PxqJERDQszwYz1BF40D-Ej1cBwYi8CnFpGfL7p8MTSIA__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44051709/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44051709/mini_magick20220711-1586-17v6hem.png?1657603043"}],"has_pdf":true,"has_fulltext":true,"page_count":9,"ordered_authors":[{"id":33542922,"first_name":"Philippe","last_name":"Maître","domain_name":"independent","page_name":"PhilippeMaître","display_name":"Philippe Maître","profile_url":"https://independent.academia.edu/PhilippeMa%C3%AEtre","photo":"/images/s65_no_pic.png"},{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}],"research_interests":[{"id":645605,"name":"THEORETICAL AND COMPUTATIONAL CHEMISTRY","url":"https://www.academia.edu/Documents/in/THEORETICAL_AND_COMPUTATIONAL_CHEMISTRY","nofollow":true}],"publication_year":2006,"publication_year_with_fallback":2006,"paper_rank":null,"all_time_views":58,"active_discussion":{}}, }) } })();</script></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653400" data-work_id="14653400" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653400/Chemistry_of_protonated_species_in_gaseous_environments">Chemistry of protonated species in gaseous environments</a></div></div><div class="u-pb4x u-mt3x"></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653400" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="f953892ee556c8d43cd1b7d47df6afcd" rel="nofollow" data-download="{"attachment_id":44006316,"asset_id":14653400,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm 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Chemistry","publication_with_fallback":"Journal of Physical Organic Chemistry","downloadable_attachments":[{"id":44006316,"asset_id":14653400,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://a.academia-assets.com/images/blank-paper.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006316/chin.200509287.pdf20160322-15574-fzao6e?1738303954=\u0026response-content-disposition=attachment%3B+filename%3DChemistry_of_protonated_species_in_gaseo\u0026Expires=1740762071\u0026Signature=G2bwEknOEy4FMPe~YhejtbkH2TSSmGqLxCWMExKOwQgjXAnhqmLpIqAvzatBYOLCjWa-cF0zqL9XVlmV~95h6CVss17bNf11aDI70AJGzGJexFbcTN2yEgcukZO-Rs5lEQ3Rpq-upr0jPbwdyrjLa0aw~5FjhJJaqlsP-palrJpzFzWd9PT91VZt4MVZesYwsqwVqj6PSD~vECf50GUTiKZLTbDqCMxacQ8ZTDQX50sgaSeHbyUo8CQ77IPWr6GZadjC2-pPSo-BuuvL~rzpTRMH6TsMY8hB7-oVkwMgxXRMkGBhmmhrBbhjS~P7WemjvcsljVnl5aUkSLx-jcv7JQ__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006316/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":null}],"downloadable_attachments_with_full_thumbnails":[],"has_pdf":false,"has_fulltext":false,"page_count":null,"ordered_authors":[{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}],"research_interests":[{"id":531,"name":"Organic Chemistry","url":"https://www.academia.edu/Documents/in/Organic_Chemistry","nofollow":true},{"id":3338,"name":"Physical Organic Chemistry","url":"https://www.academia.edu/Documents/in/Physical_Organic_Chemistry","nofollow":true},{"id":645605,"name":"THEORETICAL AND COMPUTATIONAL CHEMISTRY","url":"https://www.academia.edu/Documents/in/THEORETICAL_AND_COMPUTATIONAL_CHEMISTRY","nofollow":true}],"publication_year":2004,"publication_year_with_fallback":2004,"paper_rank":null,"all_time_views":8,"active_discussion":{}}, }) } })();</script></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653401" data-work_id="14653401" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653401/Interannular_proton_transfer_in_thermal_arenium_ions_from_the_gas_phase_alkylation_of_1_2_diphenylethane">Interannular proton transfer in thermal arenium ions from the gas-phase alkylation of 1,2-diphenylethane</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest">formation provided by single crystal/UHV studies can be used to improve the design and processing of CVD precursors.</div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653401" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li 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href="https://www.academia.edu/14653402/Gas_Phase_H_D_Exchange_between_Arenium_Ions_and_Selected_Bases_The_Site_of_Protonation_of_Simple_Aromatics">Gas-Phase H/D Exchange between Arenium Ions and Selected Bases. The Site of Protonation of Simple Aromatics</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">H/D exchange between arenium ions bearing various substituents (Y ) Et, Me 2 CH, CF 3 , CF 3 CO, NO 2 , Me 3 Si) on a perdeuterated ring and bases having at least one H atom at the active site are described. A radiolytic technique... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653402" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">H/D exchange between arenium ions bearing various substituents (Y ) Et, Me 2 CH, CF 3 , CF 3 CO, NO 2 , Me 3 Si) on a perdeuterated ring and bases having at least one H atom at the active site are described. A radiolytic technique operating at atmospheric pressure and allowing the recovery of neutral end products was used. The exchange depends on features of both the base (structure, proton affinity) and the arenium ion. The elementary step for back proton transfer from the protonated base to the neutral arene has been studied by NMR analysis of the H distribution within YC 6 D 4 H. The protonation was found to involve the most basic ring positions: ortho/para for alkyl substituents (Y ) Et, Me 2 CH) and ortho/meta for electron-withdrawing substituents (Y )</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653402" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="3e3074a2c85a6f13264cb39839e890ae" rel="nofollow" data-download="{"attachment_id":44006305,"asset_id":14653402,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006305/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653402 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653402"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653402, container: ".js-paper-rank-work_14653402", }); });</script></li><li class="js-percentile-work_14653402 InlineList-item InlineList-item--bordered hidden u-tcGrayDark"><span class="percentile-widget hidden"><span class="u-mr2x percentile-widget" style="display: none">•</span><span class="u-mr2x work-percentile"></span></span><script>$(function () { var workId = 14653402; window.Academia.workPercentilesFetcher.queue(workId, function (percentileText) { var container = $(".js-percentile-work_14653402"); container.find('.work-percentile').text(percentileText.charAt(0).toUpperCase() + percentileText.slice(1)); container.find('.percentile-widget').show(); container.find('.percentile-widget').removeClass('hidden'); }); });</script></li><li class="js-view-count-work_14653402 InlineList-item InlineList-item--bordered hidden"><div><span><span class="js-view-count view-count u-mr2x" data-work-id="14653402"><i class="fa fa-spinner fa-spin"></i></span><script>$(function () { var workId = 14653402; window.Academia.workViewCountsFetcher.queue(workId, function (count) { var description = window.$h.commaizeInt(count) + " " + window.$h.pluralize(count, 'View'); $(".js-view-count[data-work-id=14653402]").text(description); $(".js-view-count-work_14653402").attr('title', description).tooltip(); }); });</script></span><script>$(function() { $(".js-view-count-work_14653402").removeClass('hidden') })</script></div></li><li class="InlineList-item u-positionRelative" style="max-width: 250px"><div class="u-positionAbsolute" data-has-card-for-ri-list="14653402"><i class="fa fa-tag InlineList-item-icon u-positionRelative"></i>  <a class="InlineList-item-text u-positionRelative">2</a>  </div><span class="InlineList-item-text u-textTruncate u-pl9x"><a class="InlineList-item-text" data-has-card-for-ri="161176" rel="nofollow" href="https://www.academia.edu/Documents/in/The">The</a>, <script data-card-contents-for-ri="161176" type="text/json">{"id":161176,"name":"The","url":"https://www.academia.edu/Documents/in/The","nofollow":true}</script><a class="InlineList-item-text" data-has-card-for-ri="260118" rel="nofollow" href="https://www.academia.edu/Documents/in/CHEMICAL_SCIENCES">CHEMICAL SCIENCES</a><script data-card-contents-for-ri="260118" type="text/json">{"id":260118,"name":"CHEMICAL SCIENCES","url":"https://www.academia.edu/Documents/in/CHEMICAL_SCIENCES","nofollow":true}</script></span></li><script>(function(){ if (true) { new Aedu.ResearchInterestListCard({ el: $('*[data-has-card-for-ri-list=14653402]'), work: {"id":14653402,"title":"Gas-Phase H/D Exchange between Arenium Ions and Selected Bases. 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u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">The gas-phase reactivity of selected ionic species with borazine and of borazine-derived ions with selected neutrals has been studied by FT-ICR and ab initio computations and related to the corresponding ion chemistry of benzene. The most... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653406" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">The gas-phase reactivity of selected ionic species with borazine and of borazine-derived ions with selected neutrals has been studied by FT-ICR and ab initio computations and related to the corresponding ion chemistry of benzene. The most basic site of borazine is at nitrogen, and its conjugate acid, H 3 B 3 N 3 H 4 + , is similar in structure to the benzenium ion, as shown by ab initio calculations. H 3 B 3 N 3 H 4 + ions undergo H/D exchange of up to four hydrogens with CD 3 OD and do not isomerize by stepwise 1,2-hydrogen shifts. Protonation at boron is calculated to be unfavored by 28 kcal/mol with respect to protonation at nitrogen. The H 4 B 3 N 3 H 3 + ions show the features of a [B 3 N 3 H 5 ‚‚‚H 2 ] + complex, prone to dissociation at room temperature. The experimental gas-phase basicity of borazine is equal to 185.0 ( 1 kcal/mol. The Lewis basicity toward Me 3 Si + places borazine into a linear correlation pertaining to model aromatic compounds. The experimental gas-phase acidity is 365.4 ( 1.5 kcal/mol. The reactions of neutral borazine with protonating, alkylating, and nitrating ions have been characterized and compared with the corresponding reactions of benzene. B 3 N 3 H 5 + ions, retaining a cyclic structure, react similarly, in some respects, as phenylium ions, C 6 H 5 + .</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653406" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="bb64f84327b31ad59b6fddfc4fcf0778" rel="nofollow" data-download="{"attachment_id":44006301,"asset_id":14653406,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006301/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653406 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653406"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653406, container: ".js-paper-rank-work_14653406", }); 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$(".js-view-count-work_14653408").removeClass('hidden') })</script></div></li><li class="InlineList-item u-positionRelative" style="max-width: 250px"><div class="u-positionAbsolute" data-has-card-for-ri-list="14653408"><i class="fa fa-tag InlineList-item-icon u-positionRelative"></i>  <a class="InlineList-item-text u-positionRelative">12</a>  </div><span class="InlineList-item-text u-textTruncate u-pl10x"><a class="InlineList-item-text" data-has-card-for-ri="522" rel="nofollow" href="https://www.academia.edu/Documents/in/Thermodynamics">Thermodynamics</a>, <script data-card-contents-for-ri="522" type="text/json">{"id":522,"name":"Thermodynamics","url":"https://www.academia.edu/Documents/in/Thermodynamics","nofollow":true}</script><a class="InlineList-item-text" data-has-card-for-ri="524" rel="nofollow" href="https://www.academia.edu/Documents/in/Analytical_Chemistry">Analytical Chemistry</a>, <script data-card-contents-for-ri="524" type="text/json">{"id":524,"name":"Analytical Chemistry","url":"https://www.academia.edu/Documents/in/Analytical_Chemistry","nofollow":true}</script><a class="InlineList-item-text" data-has-card-for-ri="4987" rel="nofollow" href="https://www.academia.edu/Documents/in/Kinetics">Kinetics</a>, <script data-card-contents-for-ri="4987" type="text/json">{"id":4987,"name":"Kinetics","url":"https://www.academia.edu/Documents/in/Kinetics","nofollow":true}</script><a class="InlineList-item-text" data-has-card-for-ri="5769" rel="nofollow" href="https://www.academia.edu/Documents/in/Mass_Spectrometry">Mass Spectrometry</a><script data-card-contents-for-ri="5769" type="text/json">{"id":5769,"name":"Mass Spectrometry","url":"https://www.academia.edu/Documents/in/Mass_Spectrometry","nofollow":true}</script></span></li><script>(function(){ if (true) { new Aedu.ResearchInterestListCard({ el: $('*[data-has-card-for-ri-list=14653408]'), work: {"id":14653408,"title":"Binding of gaseous Fe(III)-heme cation to model biological molecules: Direct association and ligand transfer reactions","created_at":"2015-08-04T07:23:13.174-07:00","owner_id":33602983,"url":"https://www.academia.edu/14653408/Binding_of_gaseous_Fe_III_heme_cation_to_model_biological_molecules_Direct_association_and_ligand_transfer_reactions","slug":"Binding_of_gaseous_Fe_III_heme_cation_to_model_biological_molecules_Direct_association_and_ligand_transfer_reactions","dom_id":"work_14653408","summary":null,"publication":"Journal of the American Society for Mass Spectrometry","publication_with_fallback":"Journal of the American Society for Mass 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Group","url":"https://www.academia.edu/Documents/in/Functional_Group"},{"id":644345,"name":"Gases","url":"https://www.academia.edu/Documents/in/Gases"},{"id":1010725,"name":"Protein Binding","url":"https://www.academia.edu/Documents/in/Protein_Binding"},{"id":1013858,"name":"Cations","url":"https://www.academia.edu/Documents/in/Cations"},{"id":1222191,"name":"Ligands","url":"https://www.academia.edu/Documents/in/Ligands"},{"id":1257960,"name":"Ferric Compounds","url":"https://www.academia.edu/Documents/in/Ferric_Compounds"}],"publication_year":2005,"publication_year_with_fallback":2005,"paper_rank":null,"all_time_views":8,"active_discussion":{}}, }) } })();</script></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653410" data-work_id="14653410" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653410/Cation_%CF%80_Interactions_in_the_Gas_Phase_Methylation_of_%CE%B1_%CF%89_Diphenylalkanes">Cation−π Interactions in the Gas Phase Methylation of α,ω-Diphenylalkanes</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">The methylation of R,ω-diphenylalkanes (C 6 H 5 (CH 2 ) n C 6 H 5 , n ) 1-6) has been performed in the gas phase using Me 2 Cl + ions as alkylating species and toluene as reference substrate. Both in radiolytic experiments at atmospheric... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653410" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">The methylation of R,ω-diphenylalkanes (C 6 H 5 (CH 2 ) n C 6 H 5 , n ) 1-6) has been performed in the gas phase using Me 2 Cl + ions as alkylating species and toluene as reference substrate. Both in radiolytic experiments at atmospheric pressure and in FT-ICR measurements at 10 -8 Torr, the selected diphenylalkanes reacted faster than toluene, the highest reactivity displayed by 1,3-diphenylpropane. The kinetic pattern of the reaction, conforming to the established scheme of an electrophilic alkylation reaction, is consistent with a rate-determining formation of the σ-complex intermediate, at variance with the tert-butylation of the same series of compounds by Me 3 C + ions, occurring at the collisional encounter rate. The kinetic features are explained by a marked effect due to the presence of the second aryl ring, providing additional stabilization of both the ion-neutral collision complex and the σ complex with respect to toluene. Both factors contribute to the δE a of ca. 8 kcal mol -1 for the competition of 1,3-diphenylpropane and toluene found in the temperature dependence study of the Me 2 Cl + reaction.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653410" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="68185630a9a79257226bd0f68432761e" rel="nofollow" data-download="{"attachment_id":44006300,"asset_id":14653410,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006300/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653410 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653410"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653410, container: ".js-paper-rank-work_14653410", }); 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$(".js-view-count[data-work-id=14653410]").text(description); $(".js-view-count-work_14653410").attr('title', description).tooltip(); }); });</script></span><script>$(function() { $(".js-view-count-work_14653410").removeClass('hidden') })</script></div></li><li class="InlineList-item u-positionRelative" style="max-width: 250px"><div class="u-positionAbsolute" data-has-card-for-ri-list="14653410"><i class="fa fa-tag InlineList-item-icon u-positionRelative"></i></div><span class="InlineList-item-text u-textTruncate u-pl6x"><a class="InlineList-item-text" data-has-card-for-ri="645605" rel="nofollow" href="https://www.academia.edu/Documents/in/THEORETICAL_AND_COMPUTATIONAL_CHEMISTRY">THEORETICAL AND COMPUTATIONAL CHEMISTRY</a><script data-card-contents-for-ri="645605" type="text/json">{"id":645605,"name":"THEORETICAL AND COMPUTATIONAL CHEMISTRY","url":"https://www.academia.edu/Documents/in/THEORETICAL_AND_COMPUTATIONAL_CHEMISTRY","nofollow":true}</script></span></li><script>(function(){ if (false) { new Aedu.ResearchInterestListCard({ el: $('*[data-has-card-for-ri-list=14653410]'), work: {"id":14653410,"title":"Cation−π Interactions in the Gas Phase Methylation of α,ω-Diphenylalkanes","created_at":"2015-08-04T07:23:13.940-07:00","owner_id":33602983,"url":"https://www.academia.edu/14653410/Cation_%CF%80_Interactions_in_the_Gas_Phase_Methylation_of_%CE%B1_%CF%89_Diphenylalkanes","slug":"Cation_π_Interactions_in_the_Gas_Phase_Methylation_of_α_ω_Diphenylalkanes","dom_id":"work_14653410","summary":"The methylation of R,ω-diphenylalkanes (C 6 H 5 (CH 2 ) n C 6 H 5 , n ) 1-6) has been performed in the gas phase using Me 2 Cl + ions as alkylating species and toluene as reference substrate. Both in radiolytic experiments at atmospheric pressure and in FT-ICR measurements at 10 -8 Torr, the selected diphenylalkanes reacted faster than toluene, the highest reactivity displayed by 1,3-diphenylpropane. The kinetic pattern of the reaction, conforming to the established scheme of an electrophilic alkylation reaction, is consistent with a rate-determining formation of the σ-complex intermediate, at variance with the tert-butylation of the same series of compounds by Me 3 C + ions, occurring at the collisional encounter rate. The kinetic features are explained by a marked effect due to the presence of the second aryl ring, providing additional stabilization of both the ion-neutral collision complex and the σ complex with respect to toluene. Both factors contribute to the δE a of ca. 8 kcal mol -1 for the competition of 1,3-diphenylpropane and toluene found in the temperature dependence study of the Me 2 Cl + reaction.","publication":"The Journal of Physical Chemistry A","publication_with_fallback":"The Journal of Physical Chemistry A","downloadable_attachments":[{"id":44006300,"asset_id":14653410,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44006300/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006300/jp0271920-libre.pdf20160322-10143-12k0tam?1458686661=\u0026response-content-disposition=attachment%3B+filename%3DCation__Interactions_in_the_Gas_Phase_M.pdf\u0026Expires=1741321490\u0026Signature=LFnu5npDR3BPIB8p6Rq~~qrYHpRDdZG5pblYi-AsxE1JUKOhfGItAid7VMgsqv9Z4nHI9gzBbF8JwVbLD9inVZSPyKH8W1TuQA3Hc-aEzSyD7d47bcljiZOFzcDcMzVUgGLfTYvNiTNR~bEZKT~MrTfHUf9aMk9cqwohep-KtPKBGXSeLKs-IyyeogZL1zLgorjlg0keUWTRZtRa1S1eCVBrgqtrAJ8oXp9P2uptRhhf545ekDBb47X4Xg4O7HFCO0KJB2bYh1rwRfCybAhaEGoefiUMJqRD29uBdBGdugHlVH62XMFur3yZpNObkCM0JpO~AwscwDBIniC5A~4zhg__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006300/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44006300/mini_magick20190215-23722-rl3wgc.png?1550233985"}],"downloadable_attachments_with_full_thumbnails":[{"id":44006300,"asset_id":14653410,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44006300/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006300/jp0271920-libre.pdf20160322-10143-12k0tam?1458686661=\u0026response-content-disposition=attachment%3B+filename%3DCation__Interactions_in_the_Gas_Phase_M.pdf\u0026Expires=1741321490\u0026Signature=LFnu5npDR3BPIB8p6Rq~~qrYHpRDdZG5pblYi-AsxE1JUKOhfGItAid7VMgsqv9Z4nHI9gzBbF8JwVbLD9inVZSPyKH8W1TuQA3Hc-aEzSyD7d47bcljiZOFzcDcMzVUgGLfTYvNiTNR~bEZKT~MrTfHUf9aMk9cqwohep-KtPKBGXSeLKs-IyyeogZL1zLgorjlg0keUWTRZtRa1S1eCVBrgqtrAJ8oXp9P2uptRhhf545ekDBb47X4Xg4O7HFCO0KJB2bYh1rwRfCybAhaEGoefiUMJqRD29uBdBGdugHlVH62XMFur3yZpNObkCM0JpO~AwscwDBIniC5A~4zhg__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006300/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44006300/mini_magick20190215-23722-rl3wgc.png?1550233985"}],"has_pdf":true,"has_fulltext":true,"page_count":6,"ordered_authors":[{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}],"research_interests":[{"id":645605,"name":"THEORETICAL AND COMPUTATIONAL CHEMISTRY","url":"https://www.academia.edu/Documents/in/THEORETICAL_AND_COMPUTATIONAL_CHEMISTRY","nofollow":true}],"publication_year":2003,"publication_year_with_fallback":2003,"paper_rank":null,"all_time_views":8,"active_discussion":{}}, }) } })();</script></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653412" data-work_id="14653412" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653412/Tyrosine_nitration_as_evidenced_by_IRMPD_spectroscopy">Tyrosine nitration as evidenced by IRMPD spectroscopy</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">Protonated 3-nitrotyrosine ([nitroTyr+H]+) has been investigated by collision induced dissociation at variable energy and by IR multiple photon dissociation (IRMPD) spectroscopy in conjunction with quantum chemical calculations.... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653412" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">Protonated 3-nitrotyrosine ([nitroTyr+H]+) has been investigated by collision induced dissociation at variable energy and by IR multiple photon dissociation (IRMPD) spectroscopy in conjunction with quantum chemical calculations. Ultimately, this investigation is aimed at providing a diagnostic signature of protein tyrosine nitration, a post translational modification implied in pathological states. IRMPD spectroscopy of [nitroTyr+H]+ ions has been examined in two different</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653412" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="454a2b080c617b1cadda538c77987c43" rel="nofollow" data-download="{"attachment_id":44006309,"asset_id":14653412,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006309/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653412 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653412"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653412, container: ".js-paper-rank-work_14653412", }); 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Ultimately, this investigation is aimed at providing a diagnostic signature of protein tyrosine nitration, a post translational modification implied in pathological states. IRMPD spectroscopy of [nitroTyr+H]+ ions has been examined in two different","publication":"International Journal of Mass Spectrometry","publication_with_fallback":"International Journal of Mass 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Spectrometry","url":"https://www.academia.edu/Documents/in/Tandem_Mass_Spectrometry"},{"id":240148,"name":"Hydrogen Bond","url":"https://www.academia.edu/Documents/in/Hydrogen_Bond"},{"id":326380,"name":"Liquid Chromatography / Electrospray Ionization Mass Spectrometry","url":"https://www.academia.edu/Documents/in/Liquid_Chromatography_Electrospray_Ionization_Mass_Spectrometry"},{"id":585573,"name":"Amino Acid Profile","url":"https://www.academia.edu/Documents/in/Amino_Acid_Profile"},{"id":597644,"name":"Protein Modification","url":"https://www.academia.edu/Documents/in/Protein_Modification"},{"id":1114938,"name":"Ab Initio Calculation","url":"https://www.academia.edu/Documents/in/Ab_Initio_Calculation"},{"id":1341113,"name":"Collision-induced Dissociation","url":"https://www.academia.edu/Documents/in/Collision-induced_Dissociation"}],"publication_year":2011,"publication_year_with_fallback":2011,"paper_rank":null,"all_time_views":15,"active_discussion":{}}, }) } })();</script></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653416" data-work_id="14653416" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653416/Ionic_Lewis_superacids_in_the_gas_phase_Part_4_CF_3_initiated_ion_molecule_reaction_patterns_in_the_%CE%B3_radiolysis_of_CF4_n_bases_gaseous_mixtures">Ionic Lewis superacids in the gas phase. Part 4. CF+3 initiated ion/molecule reaction patterns in the γ-radiolysis of CF4/n-bases gaseous mixtures</a></div></div><div class="u-pb4x u-mt3x"></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653416" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="6f4d71af8425f02821e375e7e95952c2" rel="nofollow" data-download="{"attachment_id":44006310,"asset_id":14653416,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006310/download_file?st=MTc0MTMxNzg5MCw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653416 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653416"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653416, container: ".js-paper-rank-work_14653416", }); });</script></li><li class="js-percentile-work_14653416 InlineList-item InlineList-item--bordered hidden u-tcGrayDark"><span class="percentile-widget hidden"><span class="u-mr2x percentile-widget" style="display: none">•</span><span class="u-mr2x work-percentile"></span></span><script>$(function () { var workId = 14653416; window.Academia.workPercentilesFetcher.queue(workId, function (percentileText) { var container = $(".js-percentile-work_14653416"); container.find('.work-percentile').text(percentileText.charAt(0).toUpperCase() + percentileText.slice(1)); container.find('.percentile-widget').show(); container.find('.percentile-widget').removeClass('hidden'); }); });</script></li><li class="js-view-count-work_14653416 InlineList-item InlineList-item--bordered hidden"><div><span><span class="js-view-count view-count u-mr2x" data-work-id="14653416"><i class="fa fa-spinner fa-spin"></i></span><script>$(function () { var workId = 14653416; window.Academia.workViewCountsFetcher.queue(workId, function (count) { var description = window.$h.commaizeInt(count) + " " + window.$h.pluralize(count, 'View'); $(".js-view-count[data-work-id=14653416]").text(description); $(".js-view-count-work_14653416").attr('title', description).tooltip(); }); });</script></span><script>$(function() { $(".js-view-count-work_14653416").removeClass('hidden') })</script></div></li></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653417" data-work_id="14653417" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653417/Ionic_Lewis_superacids_in_the_gas_phase_Part_2_Reactions_of_gaseous_CF_3_with_oxygen_bases">Ionic Lewis superacids in the gas phase. Part 2. Reactions of gaseous CF+3 with oxygen bases</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">The reactivity of the CF: cation toward some oxygen bases, i.e. HrO, CHsOH, CHsCHrOH, and FCHrCHsOH, has been investigated by Fourier-transform ion cyclotron resonance mass spectrometry. The CF: ion, while inert toward HzO, displays a... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653417" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">The reactivity of the CF: cation toward some oxygen bases, i.e. HrO, CHsOH, CHsCHrOH, and FCHrCHsOH, has been investigated by Fourier-transform ion cyclotron resonance mass spectrometry. The CF: ion, while inert toward HzO, displays a high affinity for the n-center of the selected bases, yielding the corresponding excited onium intermediate that undergoes fragmentation by predominant 0-alkyl bond cleavage, leading to CFsOH and the alkyl cation. When the alkyl moiety is CH,, a rapid F-transfer from the CFsOH to CH: takes place in the fragmentation complex prior to collapse into products. A comparison between the gas-phase reactivity of CF: and of the SiF: analogue is presented and the factors governing their different behavior toward the selected oxygen bases discussed.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653417" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="a648ddaf046a1faf4b1852e77f68191e" rel="nofollow" data-download="{"attachment_id":44006308,"asset_id":14653417,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006308/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653417 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653417"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653417, container: ".js-paper-rank-work_14653417", }); 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$(".js-view-count[data-work-id=14653417]").text(description); $(".js-view-count-work_14653417").attr('title', description).tooltip(); }); });</script></span><script>$(function() { $(".js-view-count-work_14653417").removeClass('hidden') })</script></div></li><li class="InlineList-item u-positionRelative" style="max-width: 250px"><div class="u-positionAbsolute" data-has-card-for-ri-list="14653417"><i class="fa fa-tag InlineList-item-icon u-positionRelative"></i>  <a class="InlineList-item-text u-positionRelative">3</a>  </div><span class="InlineList-item-text u-textTruncate u-pl9x"><a class="InlineList-item-text" data-has-card-for-ri="4987" rel="nofollow" href="https://www.academia.edu/Documents/in/Kinetics">Kinetics</a>, <script data-card-contents-for-ri="4987" type="text/json">{"id":4987,"name":"Kinetics","url":"https://www.academia.edu/Documents/in/Kinetics","nofollow":true}</script><a class="InlineList-item-text" data-has-card-for-ri="5769" rel="nofollow" href="https://www.academia.edu/Documents/in/Mass_Spectrometry">Mass Spectrometry</a>, <script data-card-contents-for-ri="5769" type="text/json">{"id":5769,"name":"Mass Spectrometry","url":"https://www.academia.edu/Documents/in/Mass_Spectrometry","nofollow":true}</script><a class="InlineList-item-text" data-has-card-for-ri="426306" rel="nofollow" href="https://www.academia.edu/Documents/in/Fourier_transform_ion_cyclotron_resonance">Fourier transform ion cyclotron resonance</a><script data-card-contents-for-ri="426306" type="text/json">{"id":426306,"name":"Fourier transform ion cyclotron resonance","url":"https://www.academia.edu/Documents/in/Fourier_transform_ion_cyclotron_resonance","nofollow":true}</script></span></li><script>(function(){ if (true) { new Aedu.ResearchInterestListCard({ el: $('*[data-has-card-for-ri-list=14653417]'), work: {"id":14653417,"title":"Ionic Lewis superacids in the gas phase. Part 2. Reactions of gaseous CF+3 with oxygen bases","created_at":"2015-08-04T07:23:15.299-07:00","owner_id":33602983,"url":"https://www.academia.edu/14653417/Ionic_Lewis_superacids_in_the_gas_phase_Part_2_Reactions_of_gaseous_CF_3_with_oxygen_bases","slug":"Ionic_Lewis_superacids_in_the_gas_phase_Part_2_Reactions_of_gaseous_CF_3_with_oxygen_bases","dom_id":"work_14653417","summary":"The reactivity of the CF: cation toward some oxygen bases, i.e. HrO, CHsOH, CHsCHrOH, and FCHrCHsOH, has been investigated by Fourier-transform ion cyclotron resonance mass spectrometry. The CF: ion, while inert toward HzO, displays a high affinity for the n-center of the selected bases, yielding the corresponding excited onium intermediate that undergoes fragmentation by predominant 0-alkyl bond cleavage, leading to CFsOH and the alkyl cation. When the alkyl moiety is CH,, a rapid F-transfer from the CFsOH to CH: takes place in the fragmentation complex prior to collapse into products. A comparison between the gas-phase reactivity of CF: and of the SiF: analogue is presented and the factors governing their different behavior toward the selected oxygen bases discussed.","publication":"International Journal of Mass Spectrometry and Ion Processes","publication_with_fallback":"International Journal of Mass Spectrometry and Ion Processes","downloadable_attachments":[{"id":44006308,"asset_id":14653417,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44006308/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006308/0168-1176_2893_2987085-7-libre.pdf20160322-27908-5jpso5?1458686662=\u0026response-content-disposition=attachment%3B+filename%3DIonic_Lewis_superacids_in_the_gas_phase.pdf\u0026Expires=1741321490\u0026Signature=FuLdTFrwx-eeK1l9iN67SjTEMLwfXC5CkAc8na0KMb7o-TzIiqcGG8wrvvXwBmxD-TTydvzWZKaHWYudg36bekJxOA-akk6UokBNtKxDGh6kvpPtQ00dZHpc44ipxFy0mTwvW7vvXIdyGys-vJfzkSdI7jqPg8aKiO6YOIe2fcluwdFJirqntLHyaKIm68fxLejraRWU0TugU3wnYzboVxm-wAEKKXWmFg~RLwGBR6oIkGKD3w9piCeEHlWdp~4gUJ4BAxwDuN-yZd~cY9nUxpe4evDF1qW-YAR8Sg7Cc1ztltSK0XDlPaCIdDU0pf6-W1MnJ731TY2DfMucRWyUMg__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006308/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44006308/mini_magick20190215-20799-1g6hqnb.png?1550233972"}],"downloadable_attachments_with_full_thumbnails":[{"id":44006308,"asset_id":14653417,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44006308/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006308/0168-1176_2893_2987085-7-libre.pdf20160322-27908-5jpso5?1458686662=\u0026response-content-disposition=attachment%3B+filename%3DIonic_Lewis_superacids_in_the_gas_phase.pdf\u0026Expires=1741321490\u0026Signature=FuLdTFrwx-eeK1l9iN67SjTEMLwfXC5CkAc8na0KMb7o-TzIiqcGG8wrvvXwBmxD-TTydvzWZKaHWYudg36bekJxOA-akk6UokBNtKxDGh6kvpPtQ00dZHpc44ipxFy0mTwvW7vvXIdyGys-vJfzkSdI7jqPg8aKiO6YOIe2fcluwdFJirqntLHyaKIm68fxLejraRWU0TugU3wnYzboVxm-wAEKKXWmFg~RLwGBR6oIkGKD3w9piCeEHlWdp~4gUJ4BAxwDuN-yZd~cY9nUxpe4evDF1qW-YAR8Sg7Cc1ztltSK0XDlPaCIdDU0pf6-W1MnJ731TY2DfMucRWyUMg__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006308/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44006308/mini_magick20190215-20799-1g6hqnb.png?1550233972"}],"has_pdf":true,"has_fulltext":true,"page_count":13,"ordered_authors":[{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}],"research_interests":[{"id":4987,"name":"Kinetics","url":"https://www.academia.edu/Documents/in/Kinetics","nofollow":true},{"id":5769,"name":"Mass Spectrometry","url":"https://www.academia.edu/Documents/in/Mass_Spectrometry","nofollow":true},{"id":426306,"name":"Fourier transform ion cyclotron resonance","url":"https://www.academia.edu/Documents/in/Fourier_transform_ion_cyclotron_resonance","nofollow":true}],"publication_year":1993,"publication_year_with_fallback":1993,"paper_rank":null,"all_time_views":11,"active_discussion":{}}, }) } })();</script></ul></li></ul></div></div><div class="u-borderBottom1 u-borderColorGrayLighter"><div class="clearfix u-pv7x u-mb0x js-work-card work_14653418" data-work_id="14653418" itemscope="itemscope" itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653418/Ionic_Lewis_superacids_in_the_gas_phase_Part_3_Reactions_of_gaseous_CF_3_with_nitrogen_bases">Ionic Lewis superacids in the gas phase. Part 3. Reactions of gaseous CF+3 with nitrogen bases</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">The results of a Fourier-transform ion cyclotron resonance mass spectrometric study of the gas-phase reactions of CF: ions toward a number of amines are reported and compared with those of the preceding paper. As with alcohols, the CFZ... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653418" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">The results of a Fourier-transform ion cyclotron resonance mass spectrometric study of the gas-phase reactions of CF: ions toward a number of amines are reported and compared with those of the preceding paper. As with alcohols, the CFZ ion exclusively attacks the n-center of the amine giving the corresponding excited onium intermediate that, at variance with that from alcohols, undergoes fragmentation via preferential HF elimination. This process is overwhelmed by simple electron transfer within the collision complex, when thermochemically allowed. With azetidine, pyrrolidine, and piperidine, a cycloreversion reaction in the corresponding adducts with CF: is observed as well. The reactivity pattern of CFZ towards amines has been contrasted with that of SiF:. The different behavior of the two electrophiles toward n-bases is ascribed to the much larger heterolytic bond dissociation energies of Si-X (X = F, 0, or N) compared to those of C-X. According to its reactivity properties, the CF: ion can be ranked as a gaseous "Lewis superacid" but much weaker than SiFz.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653418" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="ad566e97536fa626580694c0abb75668" rel="nofollow" data-download="{"attachment_id":44006317,"asset_id":14653418,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006317/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653418 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653418"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653418, container: ".js-paper-rank-work_14653418", }); 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Part 3. Reactions of gaseous CF+3 with nitrogen bases","created_at":"2015-08-04T07:23:15.451-07:00","owner_id":33602983,"url":"https://www.academia.edu/14653418/Ionic_Lewis_superacids_in_the_gas_phase_Part_3_Reactions_of_gaseous_CF_3_with_nitrogen_bases","slug":"Ionic_Lewis_superacids_in_the_gas_phase_Part_3_Reactions_of_gaseous_CF_3_with_nitrogen_bases","dom_id":"work_14653418","summary":"The results of a Fourier-transform ion cyclotron resonance mass spectrometric study of the gas-phase reactions of CF: ions toward a number of amines are reported and compared with those of the preceding paper. As with alcohols, the CFZ ion exclusively attacks the n-center of the amine giving the corresponding excited onium intermediate that, at variance with that from alcohols, undergoes fragmentation via preferential HF elimination. This process is overwhelmed by simple electron transfer within the collision complex, when thermochemically allowed. With azetidine, pyrrolidine, and piperidine, a cycloreversion reaction in the corresponding adducts with CF: is observed as well. The reactivity pattern of CFZ towards amines has been contrasted with that of SiF:. The different behavior of the two electrophiles toward n-bases is ascribed to the much larger heterolytic bond dissociation energies of Si-X (X = F, 0, or N) compared to those of C-X. According to its reactivity properties, the CF: ion can be ranked as a gaseous \"Lewis superacid\" but much weaker than SiFz.","publication":"International Journal of Mass Spectrometry and Ion Processes","publication_with_fallback":"International Journal of Mass Spectrometry and Ion Processes","downloadable_attachments":[{"id":44006317,"asset_id":14653418,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44006317/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006317/0168-1176_2893_2987086-8-libre.pdf20160322-15574-1s1mapi?1458686662=\u0026response-content-disposition=attachment%3B+filename%3DIonic_Lewis_superacids_in_the_gas_phase.pdf\u0026Expires=1741321491\u0026Signature=ZlOEe~swJfzpFi9GPakfQDgyFv5E4-5oajCvCIClkRUQWkLc1mhulzCswJ8fwSisViw~6jokz8nKHG0NizccB~8Md6xnJ~eE~O2AwqEb4Fb7Fu800HLGelTqnx7C-Lwvz8yhw9r8lAZR~FPbZLhV6c4YCIy8ngRUVn6Ipg47RSgcf1miE8TGdXGgPXd8o4-0WKMpkFjdySixXm2vk40PlCpXvhRDBEcSJl9DnRHbh2nUu~nGtkn0MAZwK7xr92MBFTY8PqBbJ7806xETUdH941cTLHJZb~ixHsp9wac2lwtvpf8XRJ9sj7muYA8ILg21BGBfMXkvBWSPHQMLIzg9rg__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006317/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44006317/mini_magick20190215-18016-13rdr4l.png?1550233971"}],"downloadable_attachments_with_full_thumbnails":[{"id":44006317,"asset_id":14653418,"asset_type":"Work","always_allow_download":false,"scribd_thumbnail_url":"https://attachments.academia-assets.com/44006317/thumbnails/1.jpg","download_url":"https://d1wqtxts1xzle7.cloudfront.net/44006317/0168-1176_2893_2987086-8-libre.pdf20160322-15574-1s1mapi?1458686662=\u0026response-content-disposition=attachment%3B+filename%3DIonic_Lewis_superacids_in_the_gas_phase.pdf\u0026Expires=1741321491\u0026Signature=ZlOEe~swJfzpFi9GPakfQDgyFv5E4-5oajCvCIClkRUQWkLc1mhulzCswJ8fwSisViw~6jokz8nKHG0NizccB~8Md6xnJ~eE~O2AwqEb4Fb7Fu800HLGelTqnx7C-Lwvz8yhw9r8lAZR~FPbZLhV6c4YCIy8ngRUVn6Ipg47RSgcf1miE8TGdXGgPXd8o4-0WKMpkFjdySixXm2vk40PlCpXvhRDBEcSJl9DnRHbh2nUu~nGtkn0MAZwK7xr92MBFTY8PqBbJ7806xETUdH941cTLHJZb~ixHsp9wac2lwtvpf8XRJ9sj7muYA8ILg21BGBfMXkvBWSPHQMLIzg9rg__\u0026Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA","download_file_url":"https://www.academia.edu/attachments/44006317/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&","full_thumbnail_url":"https://0.academia-photos.com/attachment_thumbnails/44006317/mini_magick20190215-18016-13rdr4l.png?1550233971"}],"has_pdf":true,"has_fulltext":true,"page_count":10,"ordered_authors":[{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria 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itemtype="https://schema.org/ScholarlyArticle"><div class="header"><div class="title u-fontSerif u-fs22 u-lineHeight1_3"><a class="u-tcGrayDarkest js-work-link" href="https://www.academia.edu/14653422/_Arene_Me3C_non_covalent_complexes_in_the_gas_phase_trifluoro_methylation_of_tert_butyl_substituted_diphenylalkanes">[Arene·Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes</a></div></div><div class="u-pb4x u-mt3x"><div class="summary u-fs14 u-fw300 u-lineHeight1_5 u-tcGrayDarkest"><div class="summarized">The reaction of Me2 F+, MezC1 + and CF~-withp-Me3CC6H4(CH2)nC6D5 (n = 2, 3) initiates a reaction pattern whose major features are accounted for by the additional electrostatic stabilization afforded by the second (spectator) aromatic ring... <a class="more_link u-tcGrayDark u-linkUnstyled" data-container=".work_14653422" data-show=".complete" data-hide=".summarized" data-more-link-behavior="true" href="#">more</a></div><div class="complete hidden">The reaction of Me2 F+, MezC1 + and CF~-withp-Me3CC6H4(CH2)nC6D5 (n = 2, 3) initiates a reaction pattern whose major features are accounted for by the additional electrostatic stabilization afforded by the second (spectator) aromatic ring on ionic intermediates and ion-molecule complexes. The Me3C loss following CX~-(X = H, F) addition to the tertbutyl-substituted ring is significantly reduced with respect to a single-ring model substrate, p-Me3CC6H4Me. [Arene.</div></div></div><ul class="InlineList u-ph0x u-fs13"><li class="InlineList-item logged_in_only"><div class="share_on_academia_work_button"><a class="academia_share Button Button--inverseBlue Button--sm js-bookmark-button" data-academia-share="Work/14653422" data-share-source="work_strip" data-spinner="small_white_hide_contents"><i class="fa fa-plus"></i><span class="work-strip-link-text u-ml1x" data-content="button_text">Bookmark</span></a></div></li><li class="InlineList-item"><div class="download"><a id="305175cadc70180a3d5609217087a655" rel="nofollow" data-download="{"attachment_id":44006320,"asset_id":14653422,"asset_type":"Work","always_allow_download":false,"track":null,"button_location":"work_strip","source":null,"hide_modal":null}" class="Button Button--sm Button--inverseGreen js-download-button prompt_button doc_download" href="https://www.academia.edu/attachments/44006320/download_file?st=MTc0MTMxNzg5MSw4LjIyMi4yMDguMTQ2&s=work_strip"><i class="fa fa-arrow-circle-o-down fa-lg"></i><span class="u-textUppercase u-ml1x" data-content="button_text">Download</span></a></div></li><li class="InlineList-item"><ul class="InlineList InlineList--bordered u-ph0x"><li class="InlineList-item InlineList-item--bordered"><span class="InlineList-item-text">by <span itemscope="itemscope" itemprop="author" itemtype="https://schema.org/Person"><a class="u-tcGrayDark u-fw700" data-has-card-for-user="33602983" href="https://uniroma1.academia.edu/MariaCrestoni">Maria Crestoni</a><script data-card-contents-for-user="33602983" type="text/json">{"id":33602983,"first_name":"Maria","last_name":"Crestoni","domain_name":"uniroma1","page_name":"MariaCrestoni","display_name":"Maria Crestoni","profile_url":"https://uniroma1.academia.edu/MariaCrestoni","photo":"/images/s65_no_pic.png"}</script></span></span></li><li class="js-paper-rank-work_14653422 InlineList-item InlineList-item--bordered hidden"><span class="js-paper-rank-view hidden u-tcGrayDark" data-paper-rank-work-id="14653422"><i class="u-m1x fa fa-bar-chart"></i><strong class="js-paper-rank"></strong></span><script>$(function() { new Works.PaperRankView({ workId: 14653422, container: ".js-paper-rank-work_14653422", }); 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