Aza analogs of nucleic acid bases: infrared and Raman spectra of 5-azauracil and crystal structure of 5-azauracil monohydrate

Potter, Brian S.; Palmer, Rex A.; Withnall, Robert; Chowdhry, Babur Z.

doi:10.1039/a804613a

Cited by 6 publications

(8 citation statements)

References 18 publications

(8 reference statements)

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“…[34,35] In the former, the crystal-bound water molecules extensively engage in hydrogen bonding by donating two and accepting one hydrogen bond, yet at the same time establishing short orthogonal, polar contacts (d 1 = 3.14 , angle (O-C-O) = 988) to adjacent 5-azauracil molecules located on both sides of the H-O-H plane. Perpendicular short H 2 O···C=O contacts are also seen between water molecules that traverse crystals of a-l-aspartylglycine monohydrate forming channels of hydrogen-bonded chains and the amide carbonyl of the dipeptides (d 1 = 3.05 , angle (O-C-O) = 918).…”

Section: Csd Searches Ii: Aàb···c = O- Aàb···c N- and Aàb···rcnmentioning

confidence: 99%

“…Nevertheless, the large number of these contacts in highly halogenated aliphatic and aromatic hydrocarbons gives rise to a "steering effect" that determines crystal packing [44,45] and may determine mutual orientations of molecules in the crystal Figure 5. Crystal structures of a) 5-azauracil monohydrate [34] and b) al-aspartylglycine monohydrate [35] featuring short orthogonal intermolecular H 2 O···C=O contacts. Color code: C: gray; O: red; N: blue.…”

Section: Csd Searches Iii: Càx···càx-and -X···x-interactionsmentioning

confidence: 99%

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Orthogonal Multipolar Interactions in Structural Chemistry and Biology

2005

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The past few decades of molecular recognition studies have greatly enhanced our knowledge on apolar, ion-dipole, and hydrogen-bonding interactions. However, much less attention has been given to the role that multipolar interactions, in particular those with orthogonal dipolar alignment, play in organizing a crystal lattice or stabilizing complexes involving biological receptors. By using results from database mining, this review attempts to give an overview of types and structural features of these previously rather overlooked interactions. A number of illustrative examples of these interactions found in X-ray crystal structures of small molecules and protein-ligand complexes demonstrate their propensity and thus potential importance for both, chemical and biological molecular recognition processes.

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Section: Csd Searches Ii: Aàb···c = O- Aàb···c N- and Aàb···rcnmentioning

confidence: 99%

Section: Csd Searches Iii: Càx···càx-and -X···x-interactionsmentioning

confidence: 99%

Orthogonal Multipolar Interactions in Structural Chemistry and Biology

2005

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“…Anschauliche Beispiele orthogonaler H 2 O⋅⋅⋅CO‐Wechselwirkungen kommen in den Kristallstrukturen von 5‐Azauracil‐Monohydrat und α‐ L ‐Aspartylglycin‐Monohydrat zum Vorschein (Abbildung 5a, b) 34. 35 In der ersten Struktur sind die Kristallwassermoleküle Teil eines Geflechtes von H‐Brücken, indem sie beide Protonen für H‐Brücken bereitstellen und über ein freies Elektronenpaar zur Bildung einer weiteren H‐Brücke beitragen.…”

Section: Multipolare Wechselwirkungen Kleiner Moleküleunclassified

Orthogonale multipolare Wechselwirkungen in chemischen und biologischen Strukturen

2005

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Eine Vielzahl von Studien zur molekularen Erkennung hat unser Wissen über apolare und durch H‐Brücken vermittelte Wechselwirkungen sowie Wechselwirkungen zwischen Ionen und Dipolen in den letzten Jahrzehnten beträchtlich erweitert. Weit weniger Beachtung wurde hingegen der Rolle multipolarer Wechselwirkungen (insbesondere solcher mit orthogonaler Anordnung) beim Aufbau eines Kristallgitters oder bei der Stabilisierung von Komplexen biologischer Rezeptoren geschenkt. Das Ziel dieses Aufsatzes ist es daher, anhand von Ergebnissen aus Datenbankrecherchen eine Übersicht über die unterschiedlichen Typen dieser bislang oft übersehenen Wechselwirkungen und ihre strukturellen Charakteristiken zu geben. Die vielen Beispiele solcher Wechselwirkungen, die in Kristallstrukturen kleiner Moleküle und Protein‐Ligand‐Komplexen identifiziert wurden, sind ein Beleg für ihre Bedeutung bei molekularen Erkennungsprozessen in der Chemie und der Biologie.

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“…It can be assumed for these compounds that the water cannot be easily removed from the positions it occupies and that its removal results in the destruction of the crystal architecture. One example of such a hydrate is the monoclinic 5-azauracil monohydrate ( Figure 3) [27]. The water forms hydrogen bonds only to the host molecules, acting twice as donor and once as acceptor, while the next crystal plane is shifted so that the water molecules are embedded in a matrix of host molecules.…”

Section: Single Crystal X-ray Structures Of Hydratesmentioning

confidence: 99%

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

Fucke

Steed

2010

Water

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A review. Diffraction methods are a powerful tool to investigate the crystal structure of organic compounds in general and their hydrates in particular. The laboratory standard technique of single crystal X-ray diffraction gives information about the molecular conformation, packing and hydrogen bonding in the crystal structure, while powder X-ray diffraction on bulk material can trace hydration/dehydration processes and phase transitions under non-ambient conditions. Neutron diffraction is a valuable complementary technique to X-ray diffraction and gives highly accurate hydrogen atom positions due to the interaction of the radiation with the atomic nuclei.Although not yet often applied to organic hydrates, neutron single crystal and neutron powder diffraction give precise structural data on hydrogen bonding networks which will help explain why hydrates form in the first place.

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Aza analogs of nucleic acid bases: infrared and Raman spectra of 5-azauracil and crystal structure of 5-azauracil monohydrate

Cited by 6 publications

References 18 publications

Orthogonal Multipolar Interactions in Structural Chemistry and Biology

Orthogonal Multipolar Interactions in Structural Chemistry and Biology

Orthogonale multipolare Wechselwirkungen in chemischen und biologischen Strukturen

X-ray and Neutron Diffraction in the Study of Organic Crystalline Hydrates

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