DFT study about the effects of BX₃ (X = H, F, Cl and Br) derivatives on the C–H acidity enhancement

Article type: Research Article

Authors: Gholamirad, Parisa | Rouhani, Morteza^{; *}

Affiliations: Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran

Correspondence: [*] Corresponding author: Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran. Tel./Fax.: +98 21 44865100; E-mails: morteza.rouhani@alumni.znu.ac.ir, rouhani.morteza@gmail.com.

Abstract: A computational study about the effect of BX3 (X = H, F, Cl and Br) interaction in C–H acidity enhancement of some aldehyde, ketone and imine molecules is performed by B3LYP/6- 311++G(d,p) method in gas phase. The boron derivatives of model molecules show more acidity in comparison with their pure forms. This acidity improvement is attributed to the effective interaction of the C = O/C = N group with the B atom of BX3. The acidity enhancement is according to the BBr3 > BCl3 > BF3 > BH3 order which shows that boron compounds with electron withdrawing groups and especially BBr3 can be used as an effective and promising C–H activator in various organic reactions.

Keywords: Boron, C–H acidity enhancement, DFT, BX₃, computational

DOI: 10.3233/MGC-210070

Journal: Main Group Chemistry, vol. 21, no. 1, pp. 29-42, 2022