The crystal structure of acrylic acid

Higgs, Magen A.; Sass, Ronald L.

doi:10.1107/s0365110x63001717

Cited by 47 publications

(33 citation statements)

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“…2) [21]. In contrast to this findings, the analogous α,β-unsaturated carboxylic acids crystallize either in orthorhombic (C3: Ibam) [9][10][11][12], monoclinic (C4: C2/c) [13], or triclinic (C5, C6, C11, C12: P-1) [14][15][16][17] space groups. The high-pressure form of acrylic acid crystallizes in the monoclinic space group P21/c (No.…”

Section: Crystal Structurescontrasting

confidence: 45%

“…14) [12]. Bond lengths and angles in C9 and C10 resemble closely values found in other α,β-unsaturated carboxylic acids [9][10][11][12][13][14][15][16][17][18][19]. The crystal structures of C9 and C10 are characterized by carboxylic acid inversion dimers linked by pairs of O-H···O hydrogen bonds.…”

Section: Crystal Structuresmentioning

confidence: 56%

“…The crystal structures of acrylic acid (C3) [9][10][11][12], and crotonic acid (C4) [13] have been known for more than 40 years, while recently the crystal structures of four more members of α,β-unsaturated carboxylic acids, (E)-pent-2-enoic acid (C5) [14], (E)-hex-2-enoic acid (C6) [15], (E)-undec-2-enoic acid (C11) [16], and (E)-dodec-2-enoic acid (C12) [17], respectively, have been reported. In addition, two crystal structure determinations of co-crystals containing C6 are also known [18,19].…”

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Synthesis and Molecular Structures of (E)-non-2-enoic Acid and (E)-dec-2-enoic Acid

et al. 2015

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Section: Crystal Structurescontrasting

confidence: 45%

Section: Crystal Structuresmentioning

confidence: 56%

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Synthesis and Molecular Structures of (E)-non-2-enoic Acid and (E)-dec-2-enoic Acid

et al. 2015

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“…phthalic acid (Nowacki & Jaggi, 1957), benzoic acid (Sim, Robertson & Goodwin, 1955), acrylic acid (Higgs & Sass, 1963) and fumaric acid (Brown, 1966 Table 3, and the values for form I only are shown in Fig.3. Table 3.…”

Section: Unit-cell Dimensionsmentioning

confidence: 99%

The crystal structure of terephthalic acid

Bailey¹,

Brown²

1967

Acta Cryst

209

119

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NED C. WEBB AND RICHARD E. MARSH 387 C(5) and C(6) relatively large ones. The anisotropic parameters of the ruthenium atom correspond to values of B ranging from 2.8 (in a direction approximately parallel to e) to 2.0 (approximately along a). The disordered modificationof disorder was proposed by Trotter (1958) for bisindenyliron.In view of the near equality of the lengths of the c axes in the two modifications, there appears to be a simple relationship between the ordered and the disordered structures. This relationship is shown in Fig. 5.Visual intensity data for the hkO reflections of the disordered modification of bisindenylruthenium (see Experimental) were obtained from a set of Weissenberg photographs prepared with Cu Ka radiation. The Patterson projection onto (001) could be interpreted on the basis of four ruthenium atoms, each of half weight, in the unit cell; phases calculated from these ruthenium positions led to the electron-density projection shown in Fig.4. Since this projection is down a relatively short (6.2 A) axis, separate molecules must be resolved. Accordingly, it seems quite clear that each molecule can assume either of two orientations with equal probability, one orientation being related to the other by a twofold rotation about an axis perpendicular to the rings and passing approximately through the centers of the two C(8)-C (9) X-ray diffraction photographs of terephthalic acid have shown the existence of two polymorphic forms which have closely related triclinic unit-cell dimensions. The crystal structures of both these forms have been determined from two-dimensional data, and a full three-dimensional analysis, including the calculation of anisotropic temperature factors, has been carried out for one of these forms. The R index over 470 F(hkl) was 7.5 %. The bond lengths indicated a small amount of quinonoid character in the benzene ring, and a slight departure from planarity between the ring and the carboxyl groups. The molecules pack together in the crystal in systems of infinite chains linked together by double hydrogen bonds of length 2.608/~.

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“…† The formation of the 2:1 inclusion complex in the presence of disorder is analogous to that of 3 combining with acetone molecules in a 2:1 ratio. 22 In the latter case, however, 3 functions as a hydrogen donor and hydrogen bonds between the OH of 3 and CNO of acetone molecule are formed. 22 This is the first example of the isolation of the monomeric strans form of 2, although the dihedral angle between the OH and H 2 CNCH groups is a little large (46.5°), as shown in Fig.…”

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Isolation of monomeric s-trans-acrylic acid as a hydroxy host inclusion crystal showing anomalous CO stretching absorptions

Toda¹,

Tanaka²,

Koshima³

et al. 1998

Chem. Commun.

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The structure of monomeric s-trans-acrylic acid, trapped in an inclusion complex with an hydroxy host, was elucidated by X-ray analysis.Studies of the molecular conformations and rotational isomerism of organic compounds are of fundamental importance in chemical research. There has been especial interest in the conformations and rotamers of simple organic acids which can be studied readily using spectroscopic methods. For example, studies in the gas phase of the simplest organic acid, formic acid 1, show that the s-trans-1 rotamer is the predominant form. This has been characterized by microwave studies, 1-3 electron diffraction, 4-6 and IR spectroscopy. 7,8 Structural studies of strans-1 in low temperature matrices have also been accomplished. [9][10][11] The other rotamer, s-cis-1, has also been detected by microwave 12,13 and IR spectroscopy. 14 On the other hand in both the liquid and vapor phases of acrylic acid 2, the cyclic dimer s-trans-2···s-trans-2 is a major component existing in equilibrium with monomeric 2. 15 Microwave spectroscopic studies have established that in the vapor phase at low pressures, comparable amounts of s-cis-2 and s-trans-2 coexist with the dimer. 16,17 In the solid state, however, it was demonstrated that 2 exists as two different cyclic dimers, s-trans-2···s-trans-2 and s-cis-2···s-cis-2 by IR spectroscopy. 18 Finally, s-trans-2 and scis-2 have been identified by IR spectroscopy in a matrix. 19

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The crystal structure of acrylic acid

Cited by 47 publications

References 0 publications

Synthesis and Molecular Structures of (E)-non-2-enoic Acid and (E)-dec-2-enoic Acid

Synthesis and Molecular Structures of (E)-non-2-enoic Acid and (E)-dec-2-enoic Acid

The crystal structure of terephthalic acid

Isolation of monomeric s-trans-acrylic acid as a hydroxy host inclusion crystal showing anomalous CO stretching absorptions

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