Behavior of Ylides Containing N, O, and C Atoms as Hydrogen Bond Acceptors

Citations Over TimeTop 14% of 2000 papers

Abstract

The hydrogen bond (HB) basicity of a series of ylides containing nitrogen, oxygen, or carbon as heavy atoms, as well as the influence of the formation of the HB complexes on their structure, has been studied. In addition, in this paper we propose the formation of some rather strong HBs (that could be considered low-barrier hydrogen bonds, LBHBs) between ylides and different neutral molecules. The ylides chosen for the study were H3N+−N-H, Me3N+−N-H, H2O+−N-H, Me2O+−N-H, H2O+−O-, Me2O+−O-, and Me3N+−C-H2. As HB donors, classical donors such as HF, HCN, and HCCH were used. The analysis of the protonation energies of the ylides and the optimized geometries, interaction energies, and characteristics of the electron density of the complexes shows that these ylides are very good HB acceptors, forming stable complexes even with weak HB donors. With strong donors, when the proton transfer did not take place, very strong HBs were formed with quite large interaction energies and very short HB distances which could be considered as LBHBs. Moreover, we have found that the sign of the Laplacian of the electron density at the bond critical point (∇2ρBCP) and that of the energy density (HBCP) could characterize the strength of HBs. Thus, weak HBs (EI 0, and medium HBs (12.0 0 and HBCP 24.0 kcal/mol) show both ∇2ρBCP and HBCP < 0.

Related Papers

• → Infrared study of the interactions between the different kinds of water molecules present in sepiolite(1975)36 cited
• → Concentration of nitrogen molecules needed by nitrogen nanobubbles existing in bulk water(2013)23 cited
• → 4-Iodo-N-(phenylsulfonyl)benzamide hemihydrate(2017)1 cited
• → Effect of the orientation of the water molecules in the system of hydrogen bonds in the crystal hydrate of m-bromo-N?-(5-nitrofurylidene)benzohydrazide on its sensitivity to light(1990)
• Mechanism of the Ammonia Molecules Protonation on the Naturally Oxidized Silicon Surface(2015)