<scp>L</scp>-Phenylalaninium maleate

Alagar, M.; Krishnakumar, R. V.; Natarajan, S.

doi:10.1107/s1600536801015240

Cited by 16 publications

(25 citation statements)

References 5 publications

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“…It has a crystalline structure containing various types of hydrogen bonds besides the intramolecular one of interest, and molecules form crystal networks stabilized by shorter O-HÁ Á ÁO and longer N-HÁ Á ÁO hydrogen bonds between the ions. The only reported prior attempt to determine the structure of l-phenylalaninium hydrogen maleate was based on low-resolution X-ray diffraction data and resulted in an asymmetric hydrogen position in the intramolecular hydrogen bond with the O-H bond lengths 1.13/1.28 Å (Alagar et al, 2001). In a different X-ray study, reported for the racemic dl-phenylalaninium hydrogen maleate, all the hydrogen atoms were positioned geometrically, which led to an even more asymmetric hydrogen bond (Rajagopal et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Hirshfeld atom refinement for modelling strong hydrogen bonds

Woińska

Jayatilaka

Spackman

et al. 2014

Acta Crystallogr A Found Adv

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High-resolution low-temperature synchrotron X-ray diffraction data of the salt L-phenylalaninium hydrogen maleate are used to test the new automated iterative Hirshfeld atom refinement (HAR) procedure for the modelling of strong hydrogen bonds. The HAR models used present the first examples of Z' > 1 treatments in the framework of wavefunction-based refinement methods. L-Phenylalaninium hydrogen maleate exhibits several hydrogen bonds in its crystal structure, of which the shortest and the most challenging to model is the O-H...O intramolecular hydrogen bond present in the hydrogen maleate anion (O...O distance is about 2.41 Å). In particular, the reconstruction of the electron density in the hydrogen maleate moiety and the determination of hydrogen-atom properties [positions, bond distances and anisotropic displacement parameters (ADPs)] are the focus of the study. For comparison to the HAR results, different spherical (independent atom model, IAM) and aspherical (free multipole model, MM; transferable aspherical atom model, TAAM) X-ray refinement techniques as well as results from a low-temperature neutron-diffraction experiment are employed. Hydrogen-atom ADPs are furthermore compared to those derived from a TLS/rigid-body (SHADE) treatment of the X-ray structures. The reference neutron-diffraction experiment reveals a truly symmetric hydrogen bond in the hydrogen maleate anion. Only with HAR is it possible to freely refine hydrogen-atom positions and ADPs from the X-ray data, which leads to the best electron-density model and the closest agreement with the structural parameters derived from the neutron-diffraction experiment, e.g. the symmetric hydrogen position can be reproduced. The multipole-based refinement techniques (MM and TAAM) yield slightly asymmetric positions, whereas the IAM yields a significantly asymmetric position.

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Section: Introductionmentioning

confidence: 99%

Hirshfeld atom refinement for modelling strong hydrogen bonds

Woińska

Jayatilaka

Spackman

et al. 2014

Acta Crystallogr A Found Adv

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“…3 in Natarajan et al (2008) a C 3 3 (17) motif can be seen. References: (1) Rajagopal, Krishnakumar, Mostad & Natarajan (2001); (2) Alagar et al (2001a); (3) Alagar et al (2001b); (4) Alagar et al (2003); (5) Alagar et al (2001c); (6) and (7) Arkhipov et al (2013); (8) Alagar et al (2002); (9) Ilczyszyn et al (2003); (10) and (17) Fleck et al (2013); (11) Rajagopal et al (2004); (12) ; (13) and (18) Pratap et al (2000); (14) crystallizes from solution, but another salt in the presumable 1:1 ratio, which we have defined as (III) 0 . The formation of (III) 0 was complete, with no peaks of remaining maleic acid or of l-norvaline present in the diffraction patterns.…”

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confidence: 99%

New hydrophobicL-amino acid salts: maleates ofL-leucine,L-isoleucine andL-norvaline

et al. 2015

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Crystals of maleates of three amino acids with hydrophobic side chains [L-leucenium hydrogen maleate, C6H14NO2(+)·C4H3O4(-), (I), L-isoleucenium hydrogen maleate hemihydrate, C6H14NO2(+)·C4H3O4(-)·0.5H2O, (II), and L-norvalinium hydrogen maleate-L-norvaline (1/1), C5H11NO2(+)·C4H3O4(-)·C5H12NO2, (III)], were obtained. The new structures contain C2(2)(12) chains, or variants thereof, that are a common feature in the crystal structures of amino acid maleates. The L-leucenium salt is remarkable due to a large number of symmetrically non-equivalent units (Z' = 3). The L-isoleucenium salt is a hydrate despite the fact that L-isoleucine is a nonpolar hydrophobic amino acid (previously known amino acid maleates formed hydrates only with lysine and histidine, which are polar and hydrophilic). The L-norvalinium salt provides the first example where the dimeric cation L-Nva...L-NvaH(+) was observed. All three compounds have layered noncentrosymmetric structures. Preliminary tests have shown the presence of the second harmonic generation (SGH) effect for all three compounds.

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“…In 2ATHM, an intramolecular hydrogen bond between atoms O1 and O4 of the semimaleate anion is asymmetric and generates an S(7) motif (Bernstein et al, 1995), as observed in 8-hydroxyquinolinium hydrogen maleate (Franklin & Balasubramanian, 2009). This intramolecular hydrogen bond with an S(7) motif is a common occurrence in several salts of maleate (Alagar et al, 2001(Alagar et al, , 2002Rajagopal et al, 2001Rajagopal et al, , 2002. The corresponding intramolecular hydrogen bond with an S(5) motif is found in the semifumarate anion of 8-hydroxyquinolinium hydrogen fumarate (Franklin & Balasubramanian, 2009) but is not observed here in the semifumarate anions of 2ATHF.…”

Section: Figurementioning

confidence: 90%

“…Crystal structures and hydrogen-bonding patterns of derivatives of 2-amino-1,3-thiazole have already been reported (Lynch, 2002;Lynch & McClenaghan, 2004, 2005Glidewell et al, 2004). Maleic acid, the Z isomer of butenedioic acid, is a simple building block in two-and threedimensional supramolecular architectures (Bowes et al, 2003;Jin et al, 2003), and many crystal structures of 1:1 organic salts of maleic acid with organoamines have been reported to explain their aggregation patterns and hydrogen-bonding interactions (Alagar et al, 2001;Rajagopal et al, 2001;Lah & Leban, 2003). In all such structures, the maleic acid exists in either a monoionized state or its fully deprotonated form.…”

Section: Commentmentioning

confidence: 98%

ZandEisomers of butenedioic acid with 2-amino-1,3-thiazole: 2-amino-1,3-thiazolium hydrogen maleate and 2-amino-1,3-thiazolium hydrogen fumarate

John¹,

Balasubramanian²

2010

Acta Crystallogr C

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Maleic acid and fumaric acid, the Z and E isomers of butenedioic acid, form 1:1 adducts with 2-amino-1,3-thiazole, namely 2-amino-1,3-thiazolium hydrogen maleate (2ATHM), C(3)H(5)N(2)S(+) x C(4)H(3)O(4)(-), and 2-amino-1,3-thiazolium hydrogen fumarate (2ATHF), C(3)H(5)N(2)S(+) x C(4)H(3)O(4)(-), respectively. In both compounds, protonation of the ring N atom of the 2-amino-1,3-thiazole and deprotonation of one of the carboxyl groups are observed. The asymmetric unit of 2ATHF contains three independent ion pairs. The hydrogen maleate ion of 2ATHM shows a short intramolecular O-H...O hydrogen bond with an O...O distance of 2.4663 (19) A. An extensive hydrogen-bonded network is observed in both compounds, involving N-H...O and O-H...O hydrogen bonds. 2ATHM forms two-dimensional sheets parallel to the ab plane, extending as independent parallel sheets along the c axis, whereas 2ATHF forms two-dimensional zigzag layers parallel to the bc plane, extending as independent parallel layers along the a axis.

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L-Phenylalaninium maleate

Abstract: Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.003 A Ê R factor = 0.028 wR factor = 0.078 Data-to-parameter ratio = 7.2 For details of how these key indicators were automatically derived from the article, see

Cited by 16 publications

References 5 publications

Hirshfeld atom refinement for modelling strong hydrogen bonds

Hirshfeld atom refinement for modelling strong hydrogen bonds

New hydrophobicL-amino acid salts: maleates ofL-leucine,L-isoleucine andL-norvaline

ZandEisomers of butenedioic acid with 2-amino-1,3-thiazole: 2-amino-1,3-thiazolium hydrogen maleate and 2-amino-1,3-thiazolium hydrogen fumarate

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