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1 H and 13 C NMR sectra and one‐bond 13 C, 13 C coupling constants of ( E )‐2‐alken‐4‐yn‐1‐ols, ( E )‐2‐alken‐4‐yn‐1‐yl acetates and ( E )‐2‐alken‐4‐yn‐1‐als;
Author(s) -
Poleschner Helmut,
Heydenreich Matthias
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199711)35:10<712::aid-omr159>3.0.co;2-x
Subject(s) - chemistry , coupling constant , medicinal chemistry , carbon 13 nmr , stereochemistry , particle physics , physics
13 C and some selected 1 H NMR chemical shifts of conjugated ( E )‐enynes of the type of ( E )‐2‐alken‐4‐yn‐1‐ols (RC≡CCH=CHCH 2 OH; R = H, Me, Et, n ‐Pr, n ‐Bu, SiMe 3 ), ( E )‐2‐alken‐4‐yn‐1‐yl acetates (RC≡CCH=CHCH 2 OAc; R = H, Me, Et, n ‐Pr, n ‐Bu) and ( E )‐2‐alken‐4‐yn‐1‐als (RC≡CCH=CHCH=O; R = Et, n ‐Pr) and of (2 Z ,4 E )‐deca‐2,4‐dien‐6‐yne as a conjugated ( Z , E )‐dienyne were measured. The unequivocal assignment of the 13 C NMR chemical shifts is based on the application of standard techniques such as H,H‐COSY, C,H‐COSY and APT and, above all, on the investigation of the C,C connectivities by determination of the one‐bond 13 C, 13 C coupling constants 1 J C,C . These coupling constants show typical values for the different structural fragments. The effect of increments of the alkyl group on the resonances of the acetylenic carbon atoms are compared with those of the n ‐alkynes. The shift effects observed on going from ( E )‐2‐alken‐4‐yn‐1‐ols to ( E )‐2‐alken‐4‐yn‐1‐als are discussed in comparison with results from other classes of compounds. © 1997 John Wiley & Sons, Ltd.