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Standard values of vicinal coupling constants in the assignment of relative configurations and conformational analysis of acyclic chiral carbinols and hydrocarbons
Author(s) -
Ibarra C. Alvarez,
Romo M. T. Garcia,
Perez M. S. Arias
Publication year - 1982
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270180411
Subject(s) - vicinal , diastereomer , coupling constant , chemistry , stereochemistry , order (exchange) , computational chemistry , organic chemistry , physics , quantum mechanics , finance , economics
Standard values of vicinal coupling constants are proposed in order to assign relative configuratations and analyse the conformational distribution of acyclic chiral carbinols and hydrocarbons. Thus, the assignment of relative configurations has been achieved for the diastereomeric carbinols, (2 R 4 R , 2 S 4 S )‐ and (2 R 4 S , 2 S 4 R )‐5,5‐dimethyl‐4‐phenyl‐2‐hexanol and (1 R 3 R , 1 S 3 S )‐ and (1 R 3 S , 1 S 3 R )‐1‐mesityl‐4,4‐dimethyl‐3‐phenyl‐1‐pentanol, through the analysis of the respective vicinal coupling constants and the corresponding conformational distribution. The analysis of the vicinal coupling constants allows the establishment of the monoconformational character of the (2 R 4 S , 2 S 4 R ) diastereomer in the first case and the (1 R 3 R , 1 S 3 S ) diastereomer in the second case.