title: Hydrogen bonding at C=Se acceptors in selenoureas, selenoamides and selones.
abstract: In recent years there has been considerable interest in chalcogen and hydrogen bonding involving Se atoms, but a general understanding of their nature and behaviour has yet to emerge. In the present work, the hydrogen-bonding ability and nature of Se atoms in selenourea derivatives, selenoamides and selones has been explored using analysis of the Cambridge Structural Database and ab initio calculations. In the CSD there are 70 C=Se structures forming hydrogen bonds, all of them selenourea derivatives or selenoamides. Analysis of intramolecular geometries and ab initio partial charges show that this bonding stems from resonance-induced C(δ+)=Se(δ-) dipoles, much like hydrogen bonding to C=S acceptors. C=Se acceptors are in many respects similar to C=S acceptors, with similar vdW-normalized hydrogen-bond lengths and calculated interaction strengths. The similarity between the C=S and C=Se acceptors for hydrogen bonding should inform and guide the use of C=Se in crystal engineering.
authors.affiliation: Department of Chemistry, University of Kinshasa, BP 190 Kinshasa XI, The Democratic Republic of the Congo.
authors.forename: Dikima
authors.initials: D
authors.lastname: Bibelayi
authors.affiliation: Department of Chemistry, University of Kinshasa, BP 190 Kinshasa XI, The Democratic Republic of the Congo.
authors.forename: Albert S
authors.initials: AS
authors.lastname: Lundemba
authors.affiliation: The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England.
authors.forename: Frank H
authors.initials: FH
authors.lastname: Allen
authors.affiliation: The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England.
authors.forename: Peter T A
authors.initials: PT
authors.lastname: Galek
authors.affiliation: The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England.
authors.forename: Juliette
authors.initials: J
authors.lastname: Pradon
authors.affiliation: The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England.
authors.forename: Anthony M
authors.initials: AM
authors.lastname: Reilly
authors.affiliation: The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England.
authors.forename: Colin R
authors.initials: CR
authors.lastname: Groom
authors.affiliation: Department of Chemistry, University of Kinshasa, BP 190 Kinshasa XI, The Democratic Republic of the Congo.
authors.forename: Zéphyrin G
authors.initials: ZG
authors.lastname: Yav
keywords: Cambridge Structural Database; ab initio calculations; hydrogen bonding; selenium