Inductive or Field Substituent Effect? Quantum Chemical Modeling of Interactions in 1-Monosubstituted Bicyclooctane Derivatives

Halina Szatylowicz; Tomasz Siodła; Tadeusz M Krygowski

doi:10.1021/acsomega.7b00390

Inductive or Field Substituent Effect? Quantum Chemical Modeling of Interactions in 1-Monosubstituted Bicyclooctane Derivatives

ACS Omega. 2017 May 1;2(5):1746-1749. doi: 10.1021/acsomega.7b00390. eCollection 2017 May 31.

Authors

Halina Szatylowicz¹, Tomasz Siodła², Tadeusz M Krygowski³

Affiliations

¹ Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
² Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland.
³ Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland.

Abstract

Inductive substituent constants were obtained for systems lacking the resonance effect. The application of the charge of the substituent active region concept to study the substituent effect in 1-X-substituted bicyclooctane derivatives (B3LYP/6-311++G** calculations, X = NMe₂, NH₂, OH, OMe, CH₃, H, F, Cl, CF₃, CN, CHO, COMe, CONH₂, COOH, NO₂, NO) has revealed inductive interactions, which are through bonds.