1H, 13C, 15N NMR and Theoretical Study of Protonated Carbamic Acids and Related Compounds1

Mono-O-protonated carbamic acid, mono-O-protonated N-methyl carbamate, and mono-O-protonated methyl carbamate and di-O-protonated N,N-bis(carboxyl)-1,2-diaminoethane were prepared in FSO3H/SO2ClF and FSO3H:SbF5/SO2ClF at −78 °C and were characterized by 1H, 13C, and 15N NMR spectroscopy. Persistent...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 1998-10, Vol.63 (22), p.7993-7998
Main Authors: Olah, George A, Heiner, Thomas, Rasul, Golam, Prakash, G. K. Surya
Format: Article
Language:eng ; jpn
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Mono-O-protonated carbamic acid, mono-O-protonated N-methyl carbamate, and mono-O-protonated methyl carbamate and di-O-protonated N,N-bis(carboxyl)-1,2-diaminoethane were prepared in FSO3H/SO2ClF and FSO3H:SbF5/SO2ClF at −78 °C and were characterized by 1H, 13C, and 15N NMR spectroscopy. Persistent diprotonated carbamic acid, diprotonated N-methyl carbamate, and diprotonated methyl carbamate were not observed under these conditions. The structures, energies, and 13C and 15N NMR chemical shifts of mono-, and diprotonated carbamic acids as well as other protonated species were also calculated by ab initio/IGLO/GIAO-MP2 method and compared with the experimental results.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9814804