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Methyl (Z)-2-chloro-3-(2-methoxy-carbonyl-phen-yl)prop-2-enoate
Casey J Fadgen1, Thomas L Groy, Seth D Rose
1Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287-1604, USA.
Abstract:
In the title compound, C(12)H(11)ClO(4), the propenoate C=C bond is in the Z configuration. The propenoate C=O and C=C groups are essentially coplanar [C=C-C=O torsion angle = 172.4 (3)°] with the O atom synperiplanar to the Cl atom. However, the π systems of the aromatic ring and chloro-propenoate substituent are not coplanar; the corresponding dihedral angle is 51.5 (1)°. The noncoplanarity is likely due to steric inter-actions between the propenoate H atom and the ortho-methoxy-carbonyl group on the aromatic ring. Even in the observed noncoplanar conformation, the ortho C=O to H distance (2.40 Å) is less than the sum of the van der Waals radii of O and H (2.65 Å).
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