Electron Delocalization in Aminoguanidine: A Computational Study

Bharatam, P. V., Iqbal, P., Malde, A. and Tiwari, R. (2004) Electron Delocalization in Aminoguanidine: A Computational Study. The Journal of Physical Chemistry A, 108 47: 10509-10517. doi:10.1021/jp049366e


Author Bharatam, P. V.
Iqbal, P.
Malde, A.
Tiwari, R.
Title Electron Delocalization in Aminoguanidine: A Computational Study
Journal name The Journal of Physical Chemistry A   Check publisher's open access policy
ISSN 1089-5639
Publication date 2004-01-01
Sub-type Critical review of research, literature review, critical commentary
DOI 10.1021/jp049366e
Volume 108
Issue 47
Start page 10509
End page 10517
Total pages 9
Place of publication Washington, D.C..
Publisher American Chemical Society
Language eng
Subject 030701 Quantum Chemistry
Abstract The electronic structure, intramolecular interactions, second-order delocalizations, and C−N rotational barriers in aminoguanidine have been studied using ab initio MO and density functional methods. Isomer AG1 with intramolecular hydrogen bonding has been found to be the most stable on the potential energy surface, with nine minima. The influences of the basis set, computational method, and solvent effect on relative stabilities of important isomers of aminoguanidine have been studied. Natural Population Analysis (NPA) indicates that amino substitution in guanidine leads to an increased electron delocalization from the center of the NH2 attachment to the π frame. A strong redistribution of π electron density has been observed in aminoguanidine in relation to guanidine. The protonation energy for aminoguanidine is slightly less than that of guanidine. In protonated aminoguanidine, the π delocalization is more polarized in comparison to that in protonated guanidine. NPA, HOMA, and NICS studies have been carried out to understand electron delocalization in protonated guanidine and aminoguanidine.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Critical review of research, literature review, critical commentary
Collections: Excellence in Research Australia (ERA) - Collection
School of Chemistry and Molecular Biosciences
 
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