Yanai, Hikaru; Terajima, Yoshihiko; Kleemiss, Florian; Grabowsky, Simon; Matsumoto, Takashi (2023). Reversing the Bond Length Alternation Order in Conjugated Polyenes by Substituent Effects. Chemistry: a European journal, 29(15), e202203538. Wiley 10.1002/chem.202203538
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Chemistry_A_European_J_-_2022_-_Yanai_-_Reversing_the_Bond_Length_Alternation_Order_in_Conjugated_Polyenes_by_Substituent.pdf - Accepted Version Available under License Publisher holds Copyright. Download (2MB) | Preview |
We have synthesised several push-pull substituted conjugated polyenes and determined their accurate C-C bond lengths and charge-density distribution by utilising quantum crystallographic techniques. In a series of alkene, diene, and triene bearing two (trifluoromethyl)sulfonyl (triflyl) groups on the terminal carbon atom, unique reversal of the bond-length alternation (BLA) order has been observed. This is a pronounced aberration from the molecular structure predicted by the Lewis structure-based neutral resonance structure. Such reversal of BLA order has not been observed in push-pull compounds bearing conventional electron-withdrawing groups such as carbonyl and cyano groups instead of triflyl groups. Bonding behaviour of both normal and reversed bond length alternating systems has been revealed by complementary bonding analysis using several bond descriptors based on the experimentally fitted wavefunctions.
Item Type: |
Journal Article (Original Article) |
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Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Grabowsky, Simon |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1521-3765 |
Publisher: |
Wiley |
Language: |
English |
Submitter: |
Pubmed Import |
Date Deposited: |
16 Dec 2022 12:09 |
Last Modified: |
15 Dec 2023 00:25 |
Publisher DOI: |
10.1002/chem.202203538 |
PubMed ID: |
36515459 |
Uncontrolled Keywords: |
bond alternations bond lengths complementary bonding analysis polyenes quantum crystallography |
BORIS DOI: |
10.48350/175931 |
URI: |
https://boris.unibe.ch/id/eprint/175931 |
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