Conformation of some carboxylic acids and their derivatives

Kanters, J. A.; Kroon, Jan; Peerdeman, A. F.; Schoone, J. C.

doi:10.1016/s0040-4020(01)97912-8

Cited by 68 publications

(37 citation statements)

References 19 publications

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“…While the two distances C(3)-O(1) (1.337) and C(3)-O(2) (1.214 A) corroborate this finding, the other pair C(7)-O(3) (1.292) and C(7)-O(4) (1.234 A) are closer to each other. The average C-O and C=O distances in carboxylic acids are 1.31 and 1.23 A (Kanters, Kroon, Peerdeman & Schoone, 1967). The other bond lengths in the side chain agree well with the average values found in amino acids (Marsh & Donohue, 1967).…”

Section: (B) Bond Distances and Anglessupporting

confidence: 82%

Crystal and molecular structure of L-cystine dimethyl ester dihydrochloride monohydrate

Vijayalakshmi¹,

Srinivasan²

1975

Acta Crystallogr Sect B

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CaHI6N204S2.2HC1. H20 is monoclinic, space group P21, with a = 14"80, b = 9.34, c = 5.85/~, fl= 91.47 °, Z= 2. The structure was solved by the heavy-atom method and refined by block-diagonal least-squares calculations to a final R of 0.103 for 1620 observed reflexions. The structure is stabilized by an extensive network of hydrogen bonds. The disulphide dihedral angle is 84-4 °. The helical sense of the cystinyI group in the molecule is 'left'.

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Section: (B) Bond Distances and Anglessupporting

confidence: 82%

Crystal and molecular structure of L-cystine dimethyl ester dihydrochloride monohydrate

Vijayalakshmi¹,

Srinivasan²

1975

Acta Crystallogr Sect B

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“…The group -R-C-C ~'O' where R is C, N, O or S, has been shown to have a preferred planar arrangement in the solid state (Oskarsson, 1973Dunitz & Strickler, 1968;Kanters, Kroon, Peerdeman & Schoone, 1967;Leiserowitz & Schmidt, 1965). Because of O... O repulsion this empirical rule cannot be fulfilled in the malonate ion without a severe distortion of the C-C-C angle.…”

Section: Jomentioning

confidence: 99%

The crystal structures of calcium malonate dihydrate and strontium malonate

Briggman¹,

Oskarsson²

1977

Acta Crystallogr Sect B

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CaC3H204 . 2H20 is monoclinic, space group C2/m, with a = 13.8707 (4), b = 6.8120 (2), c = 6-8040 (2) A, fl = 106.289 (4) °, Z = 4. The structure has been refined to R = 0.032. The malonate ion is coordinated to four different Ca ions forming layers that are stacked along a. The Ca ion is coordinated by six carboxylate and two water O atoms forming a distorted square antiprism. SrC3H204 is orthorhombic, space group Pnan, with a = 6.7538 (4), b = 10.6270(8), c = 12.6744 (11) A, Z = 8. The structure has been refined to R = 0-026. The compound is composed of a three-dimensional network of linked nine-coordinate Sr 2+ complexes. The coordination polyhedron is a distorted tricapped trigonal prism. It contains a six-membered chelate ring, which imposes a conformation on the malonate ion in which the C-C-C angle is 112.5 (3) °.

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“…These figures are thus in good qualitative agreement with the relative abundances of the conformations in crystals. Inspection of Table 3 shows that the well known tendency of the a-hydroxyl group to be coplanar with the carboxyl group (Jeffrey & Parry, 1952;Kanters, Kroon, Peerdeman & Schoone, 1967;Newton & Jeffrey, 1977) exists in both types I and II. On the other hand, the torsion angle around the terminal C-C bond (Z) appears to be very sensitive to the carbon-chain conformation.…”

mentioning

confidence: 99%