title: The geometry of N-hydroxymethyl compounds. Part 3: Geometries of N-(hydroxymethyl)amides related to reactivities.
abstract: Using MNDO calculations, ground state structures of 11 N-(hydroxymethyl)amides were predicted to have pyramidal nitrogens and an s-Z conformation. The results compare favourably with ab initio calculations and with X-ray data except that MNDO tends to predict twist angles around partial double bonds which are too large. A correlation was found between N-CH2OH bond length and the logarithm of the half-life under physiological conditions. MNDO ground state structures for five N-(hydroxymethyl)amide anions were calculated to have s-E conformations and their N-CH2OH bond lengths also correlated with the half-lives of the N-(hydroxymethyl)amides. These correlations may be valuable in assessing potential anti-tumour activity.
authors: Edward Davies Chemical Laboratory, University College of Wales, Dyfed, UK.
authors: W
authors: W
authors: Mallawaarachchi
authors: R J
authors: RJ
authors: Simmonds
authors: D E
authors: DE
authors: Parry
mesh_terms: D000577:Amides; D000970:Antineoplastic Agents; D055598:Chemical Phenomena; D002621:Chemistry; D005559:Formamides; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D005559:Formamides; C055906:N-hydroxymethylformamide