Hydrogen bonding in dimers of tritolyl and tritosylurea derivatives of triphenylmethanes.
The crystal structure of the homodimer formed by the tritolylurea 3a proves the existence of a belt of six bifurcated hydrogen bonds between both NH and the O=C groups of the adjacent urea residues. For the tritosylurea 3b, four additional three-center hydrogen bonds, also involving the SO2 oxygen, are found in the crystalline state. Molecular dynamics simulations in a chloroform box confirm these patterns of the hydrogen bonds and the resulting elongation of the dimer 3b. 3b in comparison to 3a x 3a. The calculated complexation energies for the three dimeric combinations are nearly identical in agreement with the simultaneous formation of heterodimer 3a x 3b in a mixture of 3a and 3b.
Rudzevich
Yuliya
Y
Abteilung Lehramt Chemie, Fachbereich Chemie, Pharmazie und Geowissenschaften, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, D-55099, Mainz, Germany.
Rudzevich
Valentyn
V
Schollmeyer
Dieter
D
Thondorf
Iris
I
Böhmer
Volker
V
D003198:Computer Simulation; D018360:Crystallography, X-Ray; D019281:Dimerization; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013816:Thermodynamics; D014320:Triphenylmethyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D014508:Urea / Q000737:chemistry*
D014320:Triphenylmethyl Compounds; C046945:triphenylmethane; D014508:Urea