Genre
- Journal Article
The crystal structure and electron density of 3-[(p-nitrophenoxy)methyl]-3-chlorodiazirine have been analyzed using single crystal X-ray diffraction at 208 K with Mo K alpha radiation to a resolution of sin(theta(max))/lambda = 1.126 Angstrom(-1). A total of 10 440 measured reflections gave 7742 unique reflections with R(m) = 0.026. A multipole atomic density model was fitted to these reflections to give an R(F) = 0.0311. The deformation density of the phenyl portion of the compound is as expected. The dynamic deformation density of the diazirine ring, however, suggests that the bonding in the three-membered ring is a combination of the classical severely-strained cr bonding system with a significant contribution of a a donation from the N=N to an sp(2) carbon. This observation is placed in the context of similar proposals for the bonding in cyclopropanes.
UNIV PRINCE EDWARD ISL, DEPT CHEM, CHARLOTTETOWN C1A 4P3, PE, CANADA. DALHOUSIE UNIV, DEPT CHEM, HALIFAX B3H 4J3, NS, CANADA.
WASHINGTON; 1155 16TH ST, NW, WASHINGTON, DC 20036
AMER CHEMICAL SOC
PT: J; CR: ALLEN FH, 1987, J CHEM SOC PERK T 2, S1 BAERT F, 1982, ACTA CRYSTALLOGR A, V38, P143 BATTAGLIA R, 1980, Z NATURFORSCH B, V35, P719 BLESSING R, ACA T, P26 CAMERON TS, 1992, J AM CHEM SOC, V114, P1889 CAMERON TS, 1994, J AM CHEM SOC, V116, P1211 CREMER D, 1985, J AM CHEM SOC, V107, P3800 CREMER D, 1985, J AM CHEM SOC, V107, P3811 DEWAR MJS, 1979, J AM CHEM SOC, V101, P783 DOMENICANO A, 1975, ACTA CRYSTALLOGR B, V31, P221 DUNITZ JD, 1983, HELV CHIM ACTA, V66, P123 HANSEN NK, 1978, ACTA CRYSTALLOGR A, V34, P909 HIRSHFELD FL, 1991, CRYST REV, V2, P169 LINDEN A, 1988, J ORG CHEM, V53, P1085 LIU MTH, 1986, J CHEM SOC PERK T 2, P211 SCHMIDT MW, 1990, QCPE B, V10, P52 SEILER P, 1988, HELV CHIM ACTA, V71, P2100 SMITH VH, 1977, ISRAEL J CHEM, V16, P87 SOUHASSOU M, 1992, J AM CHEM SOC, V114, P2371 STEINER T, 1993, ACTA CRYSTALLOGR A, V49, P379 STEVENS IDR, 1990, J CHEM SOC P2, P661 STEWART RF, 1969, J CHEM PHYS, V51, P4569 WALSH AD, 1949, T FARADAY SOC, V45, P179 WIBERG KB, 1987, J AM CHEM SOC, V109, P985; NR: 24; TC: 4; J9: J AMER CHEM SOC; PG: 7; GA: NV421
Source type: Electronic(1)
Language
- English
Subjects
- DIFFRACTION DATA
- CONFORMATION
- CRYSTAL-STRUCTURE
- 3-MEMBERED RINGS
- Chemistry, Multidisciplinary
- THEORETICAL DETERMINATION
- MOLECULAR-STRUCTURE
- BOND LENGTHS
- THERMAL-DECOMPOSITION