Title

Crystal Engineering through Halogen Bonding: Complexes of Nitrogen Heterocycles with Organic Iodides

ACS Citation

Walsh, R. D. B.; Padgett, C. W.; Metrangolo, P.; Resnati, G.; Hanks, T. W.; Pennington, W. T. Crystal Engineering through Halogen Bonding: Complexes of Nitrogen Heterocycles with Organic Iodides. Cryst. Growth Des. 2001, 1, 165-175.

Abstract

X-ray analysis has revealed that 4,4?-bipyridine, 1,2-bis(4-pyridyl)ethylene, and hexamethylenetetramine form donor?acceptor complexes with 1,4-diiodobenzene, 1,4-diiodotetrafluorobenzene, and tetraiodoethylene in which the N···I distance is longer than that for the corresponding I2 complexes. As opposed to the corresponding I2 complexes that are molecular adducts, these complexes have extended structures and longer N···I distances. Steric and electronic effects influence the strength of the N···I interaction and the crystal packing. An additional complex of 1,2-bis(4-pyridyl)ethane and 1,4-dibromotetrafluorobenzene has also been investigated for comparison of N···I and N···Br interactions. X-ray analysis has revealed that 4,4?-bipyridine, 1,2-bis(4-pyridyl)ethylene, and hexamethylenetetramine form donor?acceptor complexes with 1,4-diiodobenzene, 1,4-diiodotetrafluorobenzene, and tetraiodoethylene in which the N···I distance is longer than that for the corresponding I2 complexes. As opposed to the corresponding I2 complexes that are molecular adducts, these complexes have extended structures and longer N···I distances. Steric and electronic effects influence the strength of the N···I interaction and the crystal packing. An additional complex of 1,2-bis(4-pyridyl)ethane and 1,4-dibromotetrafluorobenzene has also been investigated for comparison of N···I and N···Br interactions.

Source Name

Crystal Growth & Design

Publication Date

1-1-2001

Volume

1

Issue

2

Page(s)

3368-3368

Document Type

Citation

Citation Type

Article