Collect. Czech. Chem. Commun.
1981, 46, 31-39
https://doi.org/10.1135/cccc19810031
Theoretical study of electron structure and stability of quasiaromatic analogues of azulene
Pavol Zahradník, Elena Ďurčíková and Jaroslav Leška
Department of Organic Chemistry, Comenius University, 816 31 Bratislava
Abstract
Semiempirical CNDO/2 method was used in the study of 23 quasiaromatic azulene analogues containing a hydrogen bridge A..H-D, where A and D denote O, NH, or S. The values of the stabilization energy, interaction energy, and changes of Wiberg's indexes suggest that the stability of the studied compounds is caused by a strong hydrogen bond as well as by a strong delocalization of the π-electron system. Derivatives in which A and D are O and NH are especially stable. Derivatives containing an oxo or thio group are preferred in tautomeric equilibriums.
