Refinement of the structure of salicylic acid

Sundaralingam, M.; Jensen, L. H.

doi:10.1107/s0365110x65002517

Cited by 197 publications

(139 citation statements)

References 2 publications

(1 reference statement)

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“…The C(13)-O(5) bond (1-362A) is very close to the observed values: 1.363(4)A in 5-methoxy-(N,N)-dimethyltryptamine hydrochloride (Falkenberg & Carlstr6m, 1971) and 1.358(4)A, in salicylic acid (Sundaralingam & Jensen, 1965). Since in these compounds the Car-O bond has some double-bond character, it is likely that the resonance form (a) contributes to the present structure.…”

Section: Bond Lengths Of the Cationsupporting

confidence: 49%

Configuration of the ring A methoxyl in delphinine and aconitine from the crystal structure of a synthetic intermediate, C22H30O5N.C2HO4

Birnbaum¹

1972

Acta Crystallogr Sect B

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The synthetic acid oxalate, CzzH30OsN.C2HO4, m.p. 189-192°C, crystallizes in the monoclinic space group C2/c, with eight molecules in a unit cell of dimensions a=23.972 (1), b= 10.346 (2), c= 18"656 (I) /~; fl=93.16 (2) °. The densities are: Dx= 1.373, Din: 1.372 g.cm -a. The structure was determined by the symbolic addition method from data collected at room temperature on a four-circle diffractometer using the 0-20 scan technique. It was refined by the block-diagonal least-squares method to R = 4.28 % for 3115 observed reflexions. Ring A occurs in the chair conformation, and the C(1)-methoxyl is in the equatorial position, cis to the nitrogen bridge. This finding makes it necessary to revise the configurations of the corresponding methoxyl groups in delphinine and aconitine. Pairs of cations are hydrogenbonded to pairs of oxalate anions, a centre of symmetry being located between each pair. Each cation is linked to two anions by one normal and two bifurcated hydrogen bonds.

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Section: Bond Lengths Of the Cationsupporting

confidence: 49%

Configuration of the ring A methoxyl in delphinine and aconitine from the crystal structure of a synthetic intermediate, C22H30O5N.C2HO4

Birnbaum¹

1972

Acta Crystallogr Sect B

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“…Similarly, the C-OS bond lengths of 1"430 (12) and 1.45 (2)/k found in the methyl sulfate (Marsau & Cam, 1973) and ethyl sulfate (Truter, 1958) anions, respectively, are not significantly different from the length of 1.43 A (Sutton, 1965) accepted for the analogous C-OH bond. Fries & Sundaralingam (1971) note that the phenolic C-OS bond in the tyrosine sulfate anion [of length 1.410 (4) A] is much longer (9.2a) than the phenolic C-OH bond in salicylic acid [of length 1.358 (4) A] (Sundaralingam & Jensen, 1965). However, a significant contributor to the state of the salicylic acid molecule is a valence-bond structure (stabilized by the ortho carboxyl group) in which the phenolic C-OH bond is shortened (see Sundaralingam & Jensen, 1965), so that another, more direct, comparison seems useful.…”

Section: /mentioning

confidence: 99%

“…Fries & Sundaralingam (1971) note that the phenolic C-OS bond in the tyrosine sulfate anion [of length 1.410 (4) A] is much longer (9.2a) than the phenolic C-OH bond in salicylic acid [of length 1.358 (4) A] (Sundaralingam & Jensen, 1965). However, a significant contributor to the state of the salicylic acid molecule is a valence-bond structure (stabilized by the ortho carboxyl group) in which the phenolic C-OH bond is shortened (see Sundaralingam & Jensen, 1965), so that another, more direct, comparison seems useful. Recently reported z----.g/, Fig.…”

Section: /mentioning

confidence: 99%

Crystal and molecular structure of barium 2-O-sulfonato-L-ascorbate dihydrate

McClelland¹

1974

Acta Crystallogr Sect B

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The crystaland molecular structure of barium 2-O-sulfonato-L-ascorbate dihydrate, Ba(C6H609S). 2H20, has been determined from three-dimensional X-ray diffractometer data. This sulfate derivative of ascorbic acid (vitamin C) crystallizes in a triclinic cell, space group P 1, with Z= 1. Cell parameters are a=5.201 (1), b=6"951 (1), c=8.732 (1)/~, a=99.54 (1), fl=93.29 (1), y=109.12 (1) °. A total of 1423 independent data were collected, and all had F2o > 10a(Fo2). The structure was solved by the heavy-atom method and refined by the full-matrix least-squares method to a final R(F) value of 0.008. With their lengths of 1.628 (2) and 1"389 (3)/~, respectively, the ester S-O bond in the sulfonatoascorbate anion is longer and the ester C-O bond is shorter than corresponding bonds in other sulfate esters. The values determined for the structural parameters of the sulfonatoascorbate anion are in good agreement with the values reported by Hvoslef [Acta Cryst. (1969). B25, 2214-2223 for the corresponding parameters in the ascorbate anion. The sulfonatoascorbate anions are linked by barium-ion coordination and a three-dimensional network of hydrogen bonds. One of the hydrogen bonds is in the edge of the bariumion coordination polyhedron.

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“…Although the angle averages are the same, the variations for the second ligand are larger. The average length of 1-32 A for the uncoordinated phenol C--O bond does not deviate significantly (>3a) from the corresponding length of 1.36 A found for salicylic acid (Sundaralingam & Jensen, 1965).…”

Section: The Salicylate Ligandsmentioning

confidence: 73%

“…In salicylic acid the plane of the carboxyl group is inclined 1.1° to the benzene plane (Sundaralingam & Jensen, 1965). The shortest contact between these ligands [O(1)...O(5)1 is 2.84 A, about twice the van der Waals radius of O reported by Pauling (1960) (2.80 A) but less than that of Bondi (1964) (3.04 A).…”

Section: The Salicylate Ligandsmentioning

confidence: 80%