𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Conformational analysis of the tropane analogue of pethidine and related compounds by 1H NMR spectroscopy

✍ Scribed by A. F. Casy; J. E. Coates

Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
426 KB
Volume
6
Category
Article
ISSN
0749-1581

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The preferred solute conformation of ethyl 3α‐phenyltropane‐3β‐carboxylate hydrochloride, the tropane analogue of pethidine, is shown to be a piperidine chair with an axial 3‐phenyl substituent by analysis of its ^1^H NMR characteristics and spectral comparisons with model compounds. Conformational studies of synthetic intermediates are also reported and favoured boat forms identified for 3α‐diphenylhydroxymethyl‐3β‐tropanol and 3α‐phenyl‐3β‐tropanyl phenyl ketone. In the hot‐plate test for analgesia performed on mice, ethyl 3α‐phenyltropane‐3β‐carboxylate is about 1·5 times as effective as pethidine.

📜 SIMILAR VOLUMES

Conformational analysis of a synthetic c
Conformational analysis of a synthetic carboxylic ionophore in solution by 1H NMR spectroscopy
✍ Hitoshi Kuboniwa; Kazuo Yamaguchi; Akira Hirao; Seiichi Nakahama; Noboru Yamazak 📂 Article 📅 1986 🏛 John Wiley and Sons 🌐 English ⚖ 428 KB

The ' H NMR spectra of the potassium salt of a synthetic polyether carboxylic ionophore, HO[CH,CH,0(1,2-C&)O],CH,(1,2-C6&)COOH (l), in CDCI, were assigned by two-dimensional NMR methods (2D chemical shift correlation and 2D NOE). The gauche conformer about the C-C bond of the 1,2-dioxyethylene group

Conformational analysis and stability of
Conformational analysis and stability of collagen peptides by CD and by 1H- and 13C-NMR spectroscopies
✍ Roberto Consonni; Lucia Zetta; Renato Longhi; Lucio Toma; Giuseppe Zanaboni; Rug 📂 Article 📅 2000 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 248 KB 👁 2 views

Four small type I collagen CNBr peptides containing complete natural sequences were purified from bovine skin and investigated by CD and 1H- and 13C-nmr spectroscopies to obtain information concerning their conformation and thermal stability. CD showed that a triple helix was formed at 10 degrees C

Spectroscopic analysis of imidazolidines
Spectroscopic analysis of imidazolidines. Part II: 1H NMR spectroscopy and conformational analysis of 1,2 and 1,3-diarylimidazolidines
✍ Alejandra Salemo; Graciela Buldain; Isabel A. Perillo 📂 Article 📅 2001 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 37 KB

## Abstract ^1^H NMR spectra of a series of 1,2 and 1,3‐diarylimidazolidines are analyzed and correlated with their conformational features. Results were interpreted on the basis of chemical shifts and coupling constants of hydrogen atoms and confirmed by ID nOe difference experiments. 1,3‐Diarylim

Conformational analysis of β-methoxyalky
Conformational analysis of β-methoxyalkylmercuric chlorides by NMR spectroscopy and extended hückel theory
✍ T. Ibusuki; Y. Saito 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 English ⚖ 496 KB

## Abstract The energy difference (Δ__E__) between the two types of rotamers of β‐methoxyethylmercuric chloride has been satisfactorily determined by only assuming the ratio of vicinal __trans__ and __gauche__ HH coupling constants. The validity of the result was confirmed by the large temperature