Formation and Reactions of Heteroaromatic Anions in the Gas Phase

Charles H. DePuy, Gerritt P. Bean, Steven R. Kass

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The gas-phase acidities of furan, thiophene,pyridine, 1-methylpyrrole, and a number of their methyl derivatives have been determined in a flowing afterglow apparatus. The △Gacid (kcal/mol) and site of deprotonation of the parent heterocycles are as follows: furan 380 ± 3 (2-position), thiophene 373 ± 3 (2-position), pyridine 384 ± 3 (3- and/or 4-position), 1-methylpyrrole 386 ± 3 (methyl group). For the methylated species studied the acidities are 2-methylfuran 377 ± 3, 2-methylthiophene 373 ± 3, 3-methylthiophene 373 ± 3, 3-methylpyridine 371 ± 3, 2-methylpyridine 370 ± 3, and 4-methylpyridine 368 ± 3. The relative acidities of the hydrogens in the other sites in these molecules have been estimated by hydrogen-deuterium exchange studies and by other chemical methods. Anions (M - 1) from these molecules have been allowed to react with N2O, O2, COS, and CS2 and the ionic products determined. The gas-phase acidities have been compared with those calculated by the semiempirical methods AMI and MNDO.

Original languageEnglish (US)
Pages (from-to)4427-4433
Number of pages7
JournalJournal of Organic Chemistry
Issue number19
StatePublished - Sep 1 1988


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