Yanai, Hikaru and Terajima, Yoshihiko and Kleemiss, Florian and Grabowsky, Simon and Matsumoto, Takashi (2023) Reversing the Bond Length Alternation Order in Conjugated Polyenes by Substituent Effects. CHEMISTRY-A EUROPEAN JOURNAL, 29 (15). e202203538. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
We have synthesised several push-pull substituted conjugated polyenes and determined their accurate C-C bond lengths and charge-density distributions by utilising quantum crystallographic techniques. In a series of alkene, dienes, 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: | Article |
|---|---|
| Uncontrolled Keywords: | NONLINEAR-OPTICAL PROPERTIES; NATURAL RESONANCE THEORY; X-RAY; PUSH-PULL; AMIDE; CONSTITUTION; DIFFRACTION; COLOR; bond alternations; bond lengths; complementary bonding analysis; polyenes; quantum crystallography |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Central Analytical Services |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Mar 2024 07:41 |
| Last Modified: | 20 Mar 2024 07:41 |
| URI: | https://pred.uni-regensburg.de/id/eprint/60231 |
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