Title

Noncovalent Interactions in 2-Mercapto-1-methylimidazole Complexes with Organic Iodides

ACS Citation

Jay, J. I.; Padgett, C. W.; Walsh, R. D. B.; Hanks, T. W.; Pennington, W. T. Noncovalent Interactions in 2-Mercapto-1-methylimidazole Complexes with Organic Iodides. Cryst. Growth Des. 2001, 1, 501-507.

Abstract

2-Mercapto-1-methylimidazole (mmim) forms complexes with organic iodides, 1,4-diiodotetrafluorobenzene (p-F4DIB), tetraiodoethylene (TIE), and 1,2-diiodotetrafluorobenzene (o-F4DIB), in which there are remarkably similar N?H-·-·-·S hydrogen bonding and S-·-·-·I halogen bonding patterns. Extended chains of alternating donor (mmim) and acceptor (p-F4DIB and TIE) molecules are formed through divalent I-·-·-·S-·-·-·I interactions. These chains are joined into double strands through N?H-·-·-·S interactions that link two mmim molecules into a dimer. In the third complex, N?H-·-·-·S bound dimers are linked into infinite chains through S-·-·-·I interactions involving a pair of o-F4DIB molecules. Thermal analysis indicates that decomposition in both of the F4DIB complexes proceeds through total loss of acceptor, while decomposition of the TIE complex involves a combination of acceptor loss and acceptor reaction. Melting in the o-F4DIB complexes appears to be preceded by a solid-state rearrangement or premelting phenomenon that is not observed in the other two complexes. Crystal data for mmim-·p-F4DIB:? monoclinic space group, C2/c (no. 15), a = 26.915(3) Ã…, b = 7.9216(6) Ã…, c = 14.2630(4) Ã…, ? = 105.618(1)-°, V = 2928.7(4) Ã…3, Z = 8, ?calc = 2.34 g/cm3. Crystal data for mmim-·TIE:? monoclinic space group, C2/c (no. 15), a = 20.1789(12) Ã…, b = 10.7824(10) Ã…, c = 14.5072(2) Ã…, ? = 118.767(1)-°, V = 2766.9(3) Ã…3, Z = 8, ?calc = 3.10 g/cm3. Crystal data for mmim-·o-F4DIB:? triclinic space group, P1? (no. 2), a = 7.4987(7) Ã…, b = 8.1906(12) Ã…, c = 11.6512(12) Ã…, α = 83.245(4)-°, ? = 84.695(3)-°, ? = 86.135(3)-°, V = 706.35(14) Ã…3, Z = 2, ?calc = 2.43 g/cm3. 2-Mercapto-1-methylimidazole (mmim) forms complexes with organic iodides, 1,4-diiodotetrafluorobenzene (p-F4DIB), tetraiodoethylene (TIE), and 1,2-diiodotetrafluorobenzene (o-F4DIB), in which there are remarkably similar N?H-·-·-·S hydrogen bonding and S-·-·-·I halogen bonding patterns. Extended chains of alternating donor (mmim) and acceptor (p-F4DIB and TIE) molecules are formed through divalent I-·-·-·S-·-·-·I interactions. These chains are joined into double strands through N?H-·-·-·S interactions that link two mmim molecules into a dimer. In the third complex, N?H-·-·-·S bound dimers are linked into infinite chains through S-·-·-·I interactions involving a pair of o-F4DIB molecules. Thermal analysis indicates that decomposition in both of the F4DIB complexes proceeds through total loss of acceptor, while decomposition of the TIE complex involves a combination of acceptor loss and acceptor reaction. Melting in the o-F4DIB complexes appears to be preceded by a solid-state rearrangement or premelting phenomenon that is not observed in the other two complexes. Crystal data for mmim-·p-F4DIB:? monoclinic space group, C2/c (no. 15), a = 26.915(3) Ã…, b = 7.9216(6) Ã…, c = 14.2630(4) Ã…, ? = 105.618(1)-°, V = 2928.7(4) Ã…3, Z = 8, ?calc = 2.34 g/cm3. Crystal data for mmim-·TIE:? monoclinic space group, C2/c (no. 15), a = 20.1789(12) Ã…, b = 10.7824(10) Ã…, c = 14.5072(2) Ã…, ? = 118.767(1)-°, V = 2766.9(3) Ã…3, Z = 8, ?calc = 3.10 g/cm3. Crystal data for mmim-·o-F4DIB:? triclinic space group, P1? (no. 2), a = 7.4987(7) Ã…, b = 8.1906(12) Ã…, c = 11.6512(12) Ã…, α = 83.245(4)-°, ? = 84.695(3)-°, ? = 86.135(3)-°, V = 706.35(14) Ã…3, Z = 2, ?calc = 2.43 g/cm3.

Source Name

Crystal Growth & Design

Publication Date

1-1-2001

Volume

1

Issue

6

Page(s)

11452-11454

Document Type

Citation

Citation Type

Article