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Solvent Effects on the Optical Rotation of (S)-(-)-alpha-methylbenzylamine

Solvent Effects on the Optical Rotation of (S)-(-)-alpha-methylbenzylamine

Andrew T Fischer, Robert N Compton, Richard M Pagni

J Phys Chem A. 2006 Jun 8;110(22):7067-71.

PMID: 16737254

Abstract:

The optical rotation of (S)-(-)-alpha-methylbenzylamine at 589 nm has been measured in 39 different solvents at five different concentrations: 0.25, 0.50, 1.00, 2.00, and 3.00 M. A correlation of the intrinsic rotations (i.e., extrapolation of specific rotations to zero concentration) with Kamlet's and Taft's solvent parameters (alpha, beta, and pi) is established. The polarity/polarizability, pi, and solvent acidity, alpha, terms are found to have a greater effect upon the optical rotation than the basicity of the solvent, beta. The specific rotation for (S)-(-)-alpha-methylbenzylamine has been calculated with Gaussian03 using a PCM model (B3LYP aug-cc-pVDZ) for all 39 solvated systems. Comparisons between the experimental and calculated values show the importance of hydrogen bonding on specific rotation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2627863	(S)-(−)-α-Methylbenzylamine		2627-86-3	Price

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