Abstract
Thermal reactions of proton-bound dimers, (CH3CN)2H +, (CH3OCH3)2H +, and (CH3COCH3)2H+, were studied using a selected ion flow tube. Reactions observed include association, switching, and proton transfer. The association channel was observed only for base molecules that had hydrogen bonding protons such as NH3, CH3NH2, (CH3)2NH, and CH3OH. An association-insertion mechaniSoc was proposed in which the central proton of the symmetrically bound dimers is replaced by a protonated base, for example, NH +4 . These reactions are relatively slow, which demonstrates a central barrier along the potential energy surface. Ether-containing dimers do not demonstrate this insertion reaction, except for diethers, for example, CH3OCH2CH2OCH3, which can form stable bicyclic structures. Dimers such as (HCOOH)2H+, which possess hydrogen bonding protons in the periphery, undergo switching reactions with ammonia and no insertion.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Viggiano, A. A.; Dale, F.; Paulson, J. F. J. Chem. Phys. 1988, 88, 2469–2477.
Morris, R. A.; Viggiano, A. A.; Paulson, J. F.; Henchman, M. J. J. Am. Chem. Soc. 1991, 113, 5932–5936.
Hierl, P. M.; Ahrens, A. F.; Henchman, M.; Viggiano, A. A.; Paulson, J. F. lnt. J. Mass Spectrom. Ion Process. 1987, 81, 101–122.
Feng, W. Y.; Iraqi, M.; Lifshitz, C. J. Phys. Chem. 1993, 97, 3510–3514.
Yamabe, S.; Minato, T.; Hirao, K. Can. J. Chem. 1983, 67, 2827–2828.
Aviyente, V.; Vamali, T. J. Mol. Struct. 1992, 277, 285–292.
Drakyne, C. A.; Meet-Ner (Mautner), M.; Campbell, C. L.; Hughes, M. G.; Murphy, S. P. J. Chem. Phys. 1986, 84, 4958–4969.
Hiraoka, K.; Grimsrud, E. P.; Kebarle, P. J. Am. Chem. Soc. 1974, 96 3359–3364.
Wei, S.; Tzeng, W. B.; Castleman, A.W., Jr. J. Phys. Chem. 1991, 95, 5080–5085.
Mestdagh, J. M.; Binet, A.; Sublemontier, O. J. Phys. Chem. 1989, 93, 8300–8303.
Grimsrud, E. P.; Kebarle, P. J. Am. Chem. Soc. 1973, 95, 7939–7943.
Tzeng, W. B.; Wei, S.; Castleman, A. W., Jr. Chem. Phys. Lett. 1990, 168, 30–36.
Meot-Ner (Mautner), M. J. Am. Chem Soc. 1992, 114, 3312–3322.
Meat-Ner (Mautner), M.; Sieck, L. W. J. Am. Chenz. Soc. 1991, 113, 4448–4460.
Lias, S. G.; Liebman, J. F.; Levin, R. D. J. Phys. Chem. Ref Data 1984, 13, 695–808.
Arijs, E.; Nevejans, D.; Ingels, J. Int. J. Mass Spectrom. Ion Process. 1987, 81, 15–31.
Arnold, F.; Knop, G. Int. J. Mass Spectrom. Ion Process. 1987, 81, 33–44.
Iraqi, M.; Peres, M.; Petrank, A.; Lifshitz, C. Rapid Commun. Mass Specfrom., 1990, 4, 323–326.
Viggiano, A. A.; Morris, R. A.; Deakyne, C. A.; Dale, F.; Paulson, J. F. J. Phys. Chem. 1990, 94, 8193–8197.
Bohme, D. K. In Ionic Processes in the Gas Phase; Almoster Ferreira, M. A., ed.; Reidel: Dordrecht, 1982.
Iraqi, M.; Petrank, A.; Peres, M.; Lifshitz, C. Int. J. Mass Spectrum. Ion Process. 1990, 100, 679–691.
McEwan, M. J.; Denison, A. B.; Anicich, V. G.; Huntress, W.T., Jr., Int. I. Mass Spectrom. Ion Process. 1987, 87, 247–257.
Kofel, P.; McMahon, T. B. J. Phys. Chem. 1988, 92, 6174–6176.
Anicich, V. G.; Sen, A. D.; Huntress, W. T.; McEwan, M. J. J. Chem Phys. 1991, 94, 4189–4194.
Su, T.; Chesnavich, W. J. J. Chum. Phys. 1982, 76, 5182–5185.
Ridge, D. P. In Structure /Reactivity and Thermochemisty of Ions; Ausloos, P.; Lias, S.G., eds.; Reidel: Dordrecht, 1987, pp. 1–21.
El-Shall, M. S.; Olafsdottir, S. R.; Meot-Ner (Mautner), M.; Sieck, L. W. Chem. Phys. Left. 1991, 185, 193–198.
Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1257–1264.
Meat-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1265–1272.
Sieck, L. W.; Mautner (Meot-Ner), M. J. Phys. Chem. 1982, 86, 3646–3650.
Meot-Ner (Mautner), M. J. Phys. Chem. 1991, 95, 6580–6585.
Olmstead, W. N.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 4219–4228.
Speranza, M. Int. J. Mass. Spectrom. Ion Process. 1992, 118/ 119, 395–447.
Tzeng, W. B.; Wei, S.; Castleman, A. W., Jr. Chem. Phys. Lett. 1990, 166, 343–352.
Tzeng, W. B.; Wei, S.; Castleman, A. W., Jr. J. Phys. Chem. 1991, 95, 5757–5763.
Li, X.; Harrison, A. G. J. Am. Chem. Soc. 1993, 115, 6327–6332.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Feng, W.Y., Goldenberg, M. & Lifshitz, C. Reactions of proton-bound dimers. J Am Soc Mass Spectrom 5, 695–703 (1994). https://doi.org/10.1016/1044-0305(94)80001-4
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1016/1044-0305(94)80001-4