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• W2038528517 abstract "A combined experimental and ab initio molecular orbital study reveals the following features for the gas phase chemistry of ionized glycine (7) and its enol form (8). The enol form of the all-planar conformer 8.2 is found to be substantially more stable than its ketocounterpart 7.0 by ca. 22 kcal mole−1 (6-31G//ST0-3G and 6-31G//3-21G), in line with many other keto/enol tautomers of cation radicals. The barriers for interconverting 7 and 8 via various possible isomerization reactions were determined to be as high as 80–90 kcal mole−1, thus preventing facile interconversion. In fact, there is no experimental evidence for any mutual isomerization of 7 and 8. The preferred pathway for dissociating 7 corresponds to a CC cleavage process, whereas 8 undergoes loss of water. H2O loss from 8 is preceded by a complete exchange of the hydrogens of the amino and hydroxyl groups followed by H2O loss which is predicted to result in the formation of the as yet unknown cation radical of aminoketene (15). Water loss is subject to a kinetic isotope effect of kH/kD = 2.4. Some comparisons are made between the gas phase chemistry of 78 and its analogous acetic acid (1) and their enol form 2, which provides some insight into the effects of the NH2 function." @default.
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• W2038528517 date "1984-11-01" @default.
• W2038528517 modified "2023-10-03" @default.
• W2038528517 title "On the gas phase chemistry of ionized glycine and its enol. A combined experimental and ab initio molecular orbital study" @default.
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• W2038528517 doi "https://doi.org/10.1016/0168-1176(84)80072-5" @default.
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