Open AccessOpen-Form Configurational Isomers of a Tricyanofuran-Type Metastable-State Photoacid
Author(s) -
J.E. Arias,
David W. Richardson,
Eduardo E. Romero,
Mohamed Abdelrahim,
Parth Patel,
Florencio E. Hernández,
Karin Y. ChumbimuniTorres
Publication year - 2022
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c06623
Subject(s) - isomerization , metastability , substituent , chemistry , excited state , molecule , computational chemistry , thermal stability , photochemistry , stereochemistry , catalysis , organic chemistry , atomic physics , physics
We determine the presence of four open-form configurational isomers for an unsubstituted metastable-state photoacid (mPAH) of the tricyanofuran (TCF) type in solution, at room temperature, via 2D NMR experiments. Electronic structure calculations are carried out to predict the relative stability of the isomers found experimentally and their isomerization barriers. According to the calculated rate constants for isomerization, the molecule can freely interconvert between the open-form isomers, thereby providing a thermal pathway between the isomers that might be better suited to access the cyclized closed-form configuration and those that are not. In establishing the open form isomeric makeup of the TCF mPAH under study, this work establishes the need to consider the four isomers in further studies on the thermal and excited-state isomerization processes and substituent effect thereon.