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Interactions of Molecules with cis and trans Double Bonds: A Theoretical Study of cis ‐ and trans ‐2‐Butene
Author(s) -
Zarić Milana M.,
Bugarski Branko,
Kijevčanin Mirjana Lj.
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201500592
Subject(s) - 2 butene , molecule , chemistry , double bond , 1 butene , cis–trans isomerism , computational chemistry , stereochemistry , organic chemistry , catalysis
Noncovalent interactions of cis ‐ and trans‐ 2‐butene, as the smallest model systems of molecules with cis and trans double bonds, were studied to find potential differences in interactions of these molecules. The study was performed using quantum chemical methods including very accurate CCSD(T)/CBS method. We studied parallel and displaced parallel interactions in 2‐butene dimers, in butane dimers, and between 2‐butene and saturated butane. The results show the trend that interactions of 2‐butene with butane are the strongest, followed by interactions in butane dimers, whereas the interaction in 2‐butene dimers are the weakest. The strongest calculated interaction energy is between trans ‐2‐butene and butane, with a CCSD(T)/CBS energy of −2.80 kcal mol −1 . Interactions in cis ‐2‐butene dimers are stronger than interactions in trans ‐2‐butene dimers. Interestingly, some of the interactions involving 2‐butene are as strong as interactions in a benzene dimer. These insights into interactions of cis ‐ and trans‐ 2‐butene can improve understanding of the properties and processes that involve molecules with cis and trans double bonds, such as fatty acids and polymers.