Abstract
The relative hydrogen-bond (HB) properties of sulfoxides and selenoxides have been investigated experimentally using data retrieved from the Cambridge Structural database and theoretically through density functional calculations at the B3LYP/6-311++G(3df,3pd)//B3LYP/6-311++G(3df,3pd) level. The HB are significantly shorter (stronger) in selenoxides (d(O···H) = 1.78 (3) A) than in sulfoxides (d(O···H) = 1.85 (2) A). The HB directionalities and linearities observed in the solid state for the two functionalities are very similar. The spatial and molecular surface minima of the electrostatic potential are, respectively, 43.9 and 23.4 kJ/mol more negative in dimethyl selenoxide (DMSeO) in comparison with that in dimethyl sulfoxide (DMSO). The investigation of the S(Se)O bond's electronic structure using the Natural Bond Orbital (NBO) approach shows that negative hyperconjugation of the type nO → σ*S(Se)−C is much more important in DMSO than that in DMSeO. In the HB complexes, the NBO analysis shows competition...
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
