Anhydrides of real and hypothetical [hydroxy(R-O)iodo]benzenes.
The anhydrides of [hydroxy(methanesulfonato-O)]iodobenzene (HMIB) and [hydroxy(toluenesulfonato-O)]iodobenzene (HTIB) were prepared by drying acetonitrile solutions of the compounds. The anhydrides of the hypothetical compounds [hydroxy(chloroacetato)-O]iodobenzene and [hydroxy(iodoacetato)-O]iodobenzene were obtained from aqueous solutions. Crystallographic structures were obtained for the anhydrides, except that of HTIB. The electron-domain geometries of the I atoms vis-a-vis secondary I...O bonds were explored. The presence of delocalized bonding in groupings of O and I atoms was suggested. A linear relationship between the C-I-O angles and the I-O bond orders was observed.
Richter
Helen W
HW
Department of Chemistry, The University of Akron, Akron, Ohio 44325-3601, USA. richter@uakron.edu
Paul
Noel M
NM
Ray
Dale G
DG
Ray
Charlotte A
CA
Liable-Sands
Louise M
LM
Concolino
Tom
T
Lam
Matthew
M
Rheingold
Arnold L
AL
Koser
Gerald F
GF
Golen
James A
JA
D000812:Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D007462:Iodobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D000812:Anhydrides; D007462:Iodobenzenes; C551860:hydroxy(methanesulfonato-O)iodobenzene; C551861:hydroxy(toluenesulfonato-O)iodobenzene