On the Relative Resonance-Acceptor Abilities of CN, NO, COMe, CHO and NO2 Groups

06 May 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The relative resonance-acceptor ability based on ∆Gout is different from that based on ∆Gin for the conrotatory ring-opening of 3-carbomethoxycyclobutene bearing CN, NO, COMe, CHO and NO2 as C1-substituent. In contrast, the relative resonance-acceptor ability based on sC3C4-p*C1C2 interaction in TSout is much the same as in TSin. It matches further with the acceptor ability based on the net of sC3C4-p*C1C2 and pC1C2-s*C3C4 interactions. The overall resonance-acceptor ability is estimated to be CN < COMe < CHO < NO2 < NO from calculations at MP2/6-31+G(d,p) level of theory.


relative resonance-acceptor ability
conrotatory ring opening
Transition State
NBO interactions

Supplementary materials



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