The crystal and molecular structure of picolinamide

Takano, Tsunehiro; Sasada, Yoshio; Kakudo, Masao

doi:10.1107/s0365110x66003396

Cited by 62 publications

(67 citation statements)

References 5 publications

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“…The rigid-body vibration of the hydrogen-bonded dimer has already been reported for the crystal of picolinamide (Takano, Sasada & Kakudo, 1966). This feature of thermal motion of the present molecule is consistent with the molecular packing in the crystal as will be mentioned later.…”

Section: Thermal Motionsupporting

confidence: 71%

The crystal and molecular structure of tropolone

Shimanouchi¹,

Sasada²

1973

Acta Crystallogr Sect B

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101

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Tropolone, C7H602, crystallizes in space group P21/e, with a= 7.135, b---12.178, c= 7.122 A, fl= 99.63 ° and Z= 4. The crystal structure was solved by the symbolic addition procedure and refined by the leastsquares method to give the final R value of 0.054 for the 853 observed reflexions. The molecule is essentially planar and exhibits a slight degree of bond alternation in the seven-membered ring. The hydroxyl group makes a bifurcated hydrogen bond with carbonyl oxygen atoms, of which one branch is intramolecular and the other intermolecular. The latter intermolecular branches form a hydrogenbonded dimer. These characteristic hydrogen bonds seem to play a role in increasing the contribution from the dipolar ionic forms to the ground state of the tropolone molecule.

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Section: Thermal Motionsupporting

confidence: 71%

The crystal and molecular structure of tropolone

Shimanouchi¹,

Sasada²

1973

Acta Crystallogr Sect B

Self Cite

101

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“…The fact that the preferred crystalline arrangements in NA 22,23 and PA 24 (whose molecular structures are closely related) involve different basic units, with the centrosymmetric dimer existing in the two known crystalline modifications of PA 24 and being absent in the crystal of NA, 22,23 caught our attention and stimulated us to investigate the structures and relative energies of the relevant dimeric structures in these two molecules. The case of NA appeared particularly interesting, since it might be an exception to the general tendency of amides to form centrosymmetric dimers.…”

mentioning

confidence: 99%

“…According to previous structural studies [22][23][24] the basic units in the crystals of NA and PA are different. The NA crystal was found to be monoclinic, P2 1 /c (a = 3.98, b = 15.63, c = 9.44 Å , b = 99.01, at 295 K), with 4 molecules per unit cell.…”

mentioning

confidence: 99%

Dimer formation in nicotinamide and picolinamide in the gas and condensed phases probed by infrared spectroscopy

Borba

Albrecht

Gómez‐Zavaglia

et al. 2008

Phys. Chem. Chem. Phys.

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Aggregation of nicotinamide (3-pyridine-carboxamide; NA) and picolinamide (2-pyridinecarboxamide; PA) has been investigated by matrix-isolation, supersonic jet and neat solid state infrared spectroscopy, complemented by DFT(B3LYP)/6-311++G(d,p) calculations. For both compounds, the most stable dimeric structure was shown to be the centrosymmetric dimer where two monomers in their most stable forms establish two NHÁ Á ÁOQC hydrogen bonds. The most stable structures of monomers of NA and PA were characterized in detail experimentally by matrix-isolation spectroscopy and theoretically (at both the DFT(B3LYP)/6-311++G(d,p) and MP2/6-311++G(d,p) levels). For nicotinamide, two conformers were found in the matrices, with ca. 80% of the total population adopting the E form. The monomers and dimers of PA and NA were also investigated by infrared spectroscopy of the studied compounds seeded in supersonic jet expansions. These studies revealed that the constraints on the vibrational dynamics in the PA dimer are different from those in the NA dimer. In the PA dimer, the vibrational energy flow out of the N-H stretching mode was shown to be accelerated substantially by the presence of a secondary intramolecular hydrogen bond. In the glassy state of both compounds, the centrosymmetric dimer seems to be the prevalent structure. In the neat crystalline state (KBr pellet), picolinamide keeps this type of dimeric structure as the constituting unit, whereas nicotinamide molecules assume a different arrangement where one of the NHÁ Á ÁOQC bonds is replaced by an NHÁ Á ÁN(ring) bond. The different crystallograpic structures which were formed by the compounds are reflected in the vibrational spectra of the solids. These observations are correlated with the molecular properties of NA and PA, in particular with the greater conformational mobility of NA compared with PA. This is ascribable to the absence in the NA molecule of the intramolecular NHÁ Á ÁN (ring) interaction, which exists in PA.

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“…Mettler balance M163 ( ± 0.01 mg) and then mixed in a Retsch MM 400 ball mill, in 10 Ethanol was used, as it is a solvent of choice in pharmaceutical development: it belongs to class 3 of the residual solvents classification (low toxic potential) 42,43 , allowing also to achieve adequate drying of the solid samples at low temperatures.…”

mentioning

confidence: 99%

Co-crystals of diflunisal and isomeric pyridinecarboxamides – a thermodynamics and crystal engineering contribution

et al. 2016

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This version is available at https://strathprints.strath.ac.uk/56947/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output.1 To whom correspondence should be addressed. E-mail: antonio.evora@uc.pt Tel.: Co-crystals of diflunisal and isomeric pyridinecarboxamides a thermodynamics and crystal engineering contribution +351239854450 ABSTRACTDiflunisal is an anti-inflammatory non-steroidal drug, class II of the Biopharmaceutical Classification System, that has recently been the subject of renewed interest due to its potential use in the oral therapy of familial amyloid polyneuropathy. In this work, a thermodynamic based approach is used to investigate binary mixtures (diflunisal + picolinamide) and (diflunisal + isonicotinamide) in order to identify solid forms potentially useful to improve the biopharmaceutical performance of this active pharmaceutical ingredient.Special emphasis is put on the research of co-crystals and on the influence of structural changes in the pyridinecarboxamide co-former molecules on co-crystal formation with diflunisal. The thermodynamic based methodology described by ter Horst et al. in 2010 indicates that the formation of co-crystals is thermodynamically feasible for both systems. The binary solid-liquid phase diagrams are built and allow identifying unequivocally the formation of co-crystals of diflunisal with each of the two isomers and also their stoichiometry: 1:1, (diflunisal:co-former) in the case of pyridine-2-carboxamide, picolinamide, and 2

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The crystal and molecular structure of picolinamide

Cited by 62 publications

References 5 publications

The crystal and molecular structure of tropolone

The crystal and molecular structure of tropolone

Dimer formation in nicotinamide and picolinamide in the gas and condensed phases probed by infrared spectroscopy

Co-crystals of diflunisal and isomeric pyridinecarboxamides – a thermodynamics and crystal engineering contribution

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