Boron–nitrogen dative bond

Abstract

This study consists of the theoretical analysis of some organic molecules and their inorganic similar compounds, through substitution of two carbon atoms by boron and nitrogen atoms. The methods DFT/B3-LYP/TZVPP and CC2/TZVPP were considered. Firstly, ethane, ethene, and ethyne molecules (based on C atoms and their BN/NB analogs) were studied. These molecules were considered as a reference for the analysis of other molecules with functional groups. These molecules with functional groups are: ethanol, ethanal (and its isomer ethenol), ethanoic acid (and its isomer ethenediol), ethylamine, ethylbenzene, propane, and fluoroethane. We studied the energies, bond length, population analysis, and bond order. The dative bonds (BN) are bigger and weaker than that covalent based on C atoms. The dative bond has π character when the BN bond is double and triple. It is possible to distinguish two different behaviors for BN bonds, one when the functional group is bounded to the B atom, and the other to the N atom. When the functional group is bounded to the B atom, the BN bond is weaker and lengthier than that when the same group is bounded to the N atom. However, the isomer with weaker BN bond is the most stable one. Graphical abstract Comparative studies of dative bonds among substituted inorganic molecules, e.g., BN-ethanol, show important differences in terms of length and energy in comparison to organic analogous. There is also a difference when comparing BN or NB molecules (according to witch atom the functional group is bonded to, B or N); bond length, for example, is bigger for BN molecules.

The Change in the Nature of the Chemical Bond through Hydrogen Tunneling Process in BN‐Ethylamine

“…The BL variations are also shown in Figure 7 and Table 4. Single, double, and intermediary (between single and double) dative bonds was considered, [1,29] e. g., the dative double bond is composed by σ single covalent bond and π coordinate covalent bond. Similarly, values of bond length have been obtained by Leroy et ali.…”

“…In this paper BN‐ethylamine (NH 2 BH 2 NH 3 ) has been considered to demonstrate the bonding change from BN single covalent (…H 2 B‐N H 2 ) to coordinate covalent (dative) (…H 2 B‐N H 3 ) bonds and vice versa. This molecule is more stable than its structural isomer NH 2 NH 2 BH 3 . However, BN‐ethylamine is only weakly stable in comparison with its respective decomposition product NH 2 BH 2 + NH 3 .…”

“…Finally, we studied the interconversion of the dative bond and the usual single covalent bond. Those bonds were studied separately . However, this interconversion had not yet been studied.…”

“…This molecule is more stable than its structural isomer NH 2 NH 2 BH 3 . [1] However, BN-ethylamine is only weakly stable in comparison with its respective decomposition product NH 2 BH 2 + NH 3 . The NH 2 BH 2 NH 3 molecule is found in solid state as a di ammoniate salt of diborane ([NH 3 BH 2 NH 3 ] + [BH 4 ] -), [2,3,4] which is an important solid hydrogen storage material.…”

“…Those bonds were studied separately. [1,14,18,19,27,28] However, this interconversion had not yet been studied. In fact, the charge migration findings governed by tunneling are possibly unique to this system.…”