J. Mol. Struc.:THEOCHEM 851, 75-83 (2008)

DOI: 10.1016/j.theochem.2007.10.037

Heteropentalenes aromaticity: A theoretical study

Theoretical calculations at the B3LYP/6-311++G∗∗ level including GIAO and NICS chemical shifts have been carried out on seven simple heterocycles (furan, thiophene, pyrrole, 1H-imidazole, 1H-pyrazole, 1H-1,2,3-triazole, 2H-1,2,3-triazole) and 28 heteropentalenes (22 of them being azapentalenes). The relative energies are discussed in function of the heteroatoms and of the topology ([2,3-b] vs. [3,2-b]) for isomers and tautomers. Schleyer’s NICS(0) and NICS(1) are used to discuss the aromaticity of these compounds.