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Computational investigations of intermolecular interactions between electron-accepting bromo- and iodo-pentafluorobenzene and electron-donating furan and thiophene

Abstract

Bromo- and iodo-pentafluorobenzenes (C6F5X, X=Br, I) exhibit intriguing σ- and π-holes’ characters which are able to accept electrons, while furan (C4H4O) and thiophene (C4H4S) are able to donate electrons because of their electron-rich atom or group (i.e., O atom and π ring of C4H4O and π ring of C4H4S). Theoretical investigations of intermolecular interactions for the systems (i.e., C4H4O and C6F5Br, C4H4S and C6F5Br, C4H4O and C6F5I, C4H4S and C6F5I) have been carried out at the M06-2X/aug-cc-pVDZ and wB97-XD/aug-cc-pVDZ levels without and with counterpoise method, together with single point calculations at the CCSD(T)/aug-cc-pVDZ level. For the system of C4H4O and C6F5X (X=Br, I), five different dimers I-V and I'-V' connected by σ-hole•••n, σ-hole•••π and π-hole•••π bonds were found. While for the system of C4H4S and C6F5Br, four different dimers VI-IX connected by σ-hole•••π and π-hole•••π bonds were found. But there are five dimers VI'-X' found for the system of C4H4S and C6F5I connected by σ-hole•••π, π-hole•••π and σ-hole•••n bonds. The driving forces for the formation of these dimers were uncovered by EDA analyses. NCI, QTAIM and NBO analyses were employed to prove the existences of intermolecular interactions in these dimers and to elaborate their nature. The results presented here will be insightful for studying other intermolecular system involving σ- and π-holes.

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Publication details

The article was received on 11 Sep 2018, accepted on 09 Nov 2018 and first published on 09 Nov 2018


Article type: Paper
DOI: 10.1039/C8NJ04611E
Citation: New J. Chem., 2018, Accepted Manuscript
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    Computational investigations of intermolecular interactions between electron-accepting bromo- and iodo-pentafluorobenzene and electron-donating furan and thiophene

    F. Yang, K. Lu, X. Yang, C. Yan, R. Wang, W. Ye, P. Zhou and Z. Yang, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ04611E

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