Synthesis and conformational analysis of novel trimeric maleimide cross-linking reagents.
Nine homotrifunctional cross-linking reagents are presented. Their synthesis and chemical properties as well as their characterization by classical mechanical conformational searching techniques is reported. Mixed Low Mode and Monte Carlo searching techniques were used to exhaustively sample the OPLS2005/GBSA(water) potential energy surface of trisubstituted cyclohexane and benzene derivatives of C3 symmetry. Geometric structure, molecular length, and hydrogen-bonding patterns were analyzed. Nonaromatic compounds exhibited exclusively chair conformations at low energies, with a preference for axial or equatorial arms depending upon the presence of additional ring substituent Me groups. Increasing chain length often resulted in overall shorter molecular length due to additional chain flexibility. These results were consistent with one- and two-dimensional temperature-dependent NMR studies.
Szczepanska
Agnieszka
A
Department of Organic Chemistry, Faculty of Chemistry, University of Seville, P.O. Box 1203, E-41071 Seville, Spain.
Espartero
José Luis
JL
Moreno-Vargas
Antonio J
AJ
Carmona
Ana T
AT
Robina
Inmaculada
I
Remmert
Sarah
S
Parish
Carol
C
D000577:Amides / Q000737:chemistry; D003198:Computer Simulation; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008301:Maleimides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013696:Temperature
D000577:Amides; D003432:Cross-Linking Reagents; D008301:Maleimides; C043592:maleimide