ISSN:
0192-8651
Keywords:
Computational Chemistry and Molecular Modeling
;
Biochemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Computer Science
Notes:
Ab initio SCF molecular orbital calculations have been performed to ascertain the conformational preferences of protonated, neutral, and deprotonated amidine [HC(=NH)NH2], using the 3-21G split valence basis set. The states of eight stable species, eight transition states, and four higher-order saddle points have been determined by complete geometry optimization utilizing analytic energy gradient techniques. Protonation at the amidine =NH is preferred over the -NH2 site by 37.1 kcal/mol. Neutral amidine has rotational barriers of 9.6 and 11.7 kcal/mol for the HN=CN cis and trans isomers, respectively, while all the stable HC(NH2)2+ and HC(NH)2- species possess torsional barriers larger than 23 kcal/mol. There is, however, essentially free C - N single-bond rotation in HC(=NH)NH3+, the calculated barriers being 0.7 and 1.8 kcal/mol for the cis and trans HN=CN isomers, respectively.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jcc.540030111
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