BORONIC ACIDS AS MOLECULAR SENSORS - NBO ANALYSIS AND C-13 CHEMICAL-SHIFTS AS TOOLS FOR EVALUATION OF DFT GEOMETRY OPTIMIZATION OF COMPLEXES OF DIPHENYLMETHANE 3,3'-DIBORONIC ACIDS AND GLUCOSE
R. Uggla et al., BORONIC ACIDS AS MOLECULAR SENSORS - NBO ANALYSIS AND C-13 CHEMICAL-SHIFTS AS TOOLS FOR EVALUATION OF DFT GEOMETRY OPTIMIZATION OF COMPLEXES OF DIPHENYLMETHANE 3,3'-DIBORONIC ACIDS AND GLUCOSE, Tetrahedron : asymmetry, 7(6), 1996, pp. 1741-1748
Studies on the formation of bisdentate complexes of diphenylmethane-3,
3'-diboronic acid 1 and glucose were carried out using DFT methods. A
1,2- and 5,6-coordinated complex (i.e. 2) was chosen (on the basis of
a recent NMR spectroscopic study) as a most probable model of plausibl
e isomeric structures which 1 could form as reacting with hydroxylic p
ositions (total of 5) of glucose (in the furanose form). The optimized
structure of 2 was found to be closely similar to that proposed on th
e basis of the earlier NMR study, The calculated C-13 NMR shifts were
closely similar to the measured ones. A more glucose selective analog
of the sensor 1 was proposed. Copyright (C) 1996 Elsevier Science Ltd