Development of quantum-chemical investigations of heterocycles at the Institute of Organic Chemistry, Russian Academy of Sciences (review)

Abstract

of attack by electrophile (position selectivity), relative stability of onium ions, stable thiophenium ions, their transformations.This review is dedicated to the memory of the distinguished organic chemist, one of the "founding fathers" of the journal "Chemistry of Heterocyclic Compounds", Professor, Doctor of chemical sciences, eminent man of science and technology of the RSFSR Ya. L. Gol'dfarb. As a scientist Prof. Gol'dfarb invariably showed a keen interest in all that was new and progressive in science, and the last 30 years of Yakov Lazarevich's life, when instrumental methods and theoretical concepts were being vigorously developed, were exceptionally prolific. It is no wonder that even in 1970-1971 Ya. L. Gol'dfarb became the initiator of the use of quantum-chemical methods in work at the synthesis laboratories of the N. D. Zelinsky Institute of Organic Chemistry. The possibilities of quantum-chemical methods have certainly increased substantially over the last 40 years, but the pioneering work still retains its significance in that appropriate models were carefully selected and the results of the calculations were always matched with the experimental data.Typically, the quantum-chemical calculations were no way to "dress up" the work carried out in the laboratory but were directed toward a meaningful study of the reactivity of heteroaromatic compounds, and to this day investigations are conducted with close collaboration between specialists in organic synthesis and specialists in the field of quantum chemistry. It is no coincidence that even in 1972 experimental data existing at that time on the reactivity and structure of compounds of the thiophene and furan series carrying electronaccepting substituents were being analyzed in detail on the basis of the results of quantum-chemical calculations performed at the Institute of Organic Chemistry, USSR Academy of Sciences [1], while in1977 the _______ * In happy memory of Yakov Lazarevich Gol'dfarb.