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Solid-state chemistry and polymorphism of the nucleobase adenine

Solid-state chemistry and polymorphism of the nucleobase adenine
Solid-state chemistry and polymorphism of the nucleobase adenine
The nucleobase adenine plays a pivotal role in the chemistry of life, but is also becoming increasingly interesting as a building block in the synthesis of functional solid materials. Although commercially available as a solid, adenine’s solid-state chemistry has so far been neglected. In this comprehensive study it is shown that adenine is most often marketed as a mixture of two polymorphs, one previously known, and a new polymorph. Both polymorphs exhibit layered structures with different hydrogen-bonding patterns within layers. The crystal structure of the new polymorph was elucidated using synchrotron powder X-ray diffraction. Polymorph occurrence conditions, interconversion and the difference in their thermodynamic stability were established theoretically and experimentally revealing the polymorph with Z' = 2 (known) as stable relative to the polymorph with Z' = 1 (new). The adenine layers in both polymorphs are connected by weak interaction likely resulting in stacking faults which are manifested in anisotropic line broadening of their powder diffraction patterns. Analysis of a few commercial samples of adenine revealed them all to be a polymorph mixture, which could be inconvenient in experiments where properties of the solid material could be relevant.
1528-7483
3262–3270
Stolar, Tomislav
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Lukin, Stipe
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Pozar, Josip
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Rubcic, Mirta
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Day, Graeme
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Biljan, Ivana
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Sisak Jung, Dubravka
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Horvat, Gordan
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Uzarevic, Krunoslav
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Mestrovic, Ernest
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Halasz, Ivan
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Stolar, Tomislav
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Lukin, Stipe
b111eeba-6594-41d0-9a9f-70d9564bf73d
Pozar, Josip
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Rubcic, Mirta
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Day, Graeme
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Biljan, Ivana
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Sisak Jung, Dubravka
abc16fc6-1c4d-4673-a6e9-16d77aa65002
Horvat, Gordan
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Uzarevic, Krunoslav
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Mestrovic, Ernest
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Halasz, Ivan
6b64d206-f49c-40b4-8a8b-a34eb2be6346

Stolar, Tomislav, Lukin, Stipe, Pozar, Josip, Rubcic, Mirta, Day, Graeme, Biljan, Ivana, Sisak Jung, Dubravka, Horvat, Gordan, Uzarevic, Krunoslav, Mestrovic, Ernest and Halasz, Ivan (2016) Solid-state chemistry and polymorphism of the nucleobase adenine. Crystal Growth & Design, 16 (6), 3262–3270. (doi:10.1021/acs.cgd.6b00243).

Record type: Article

Abstract

The nucleobase adenine plays a pivotal role in the chemistry of life, but is also becoming increasingly interesting as a building block in the synthesis of functional solid materials. Although commercially available as a solid, adenine’s solid-state chemistry has so far been neglected. In this comprehensive study it is shown that adenine is most often marketed as a mixture of two polymorphs, one previously known, and a new polymorph. Both polymorphs exhibit layered structures with different hydrogen-bonding patterns within layers. The crystal structure of the new polymorph was elucidated using synchrotron powder X-ray diffraction. Polymorph occurrence conditions, interconversion and the difference in their thermodynamic stability were established theoretically and experimentally revealing the polymorph with Z' = 2 (known) as stable relative to the polymorph with Z' = 1 (new). The adenine layers in both polymorphs are connected by weak interaction likely resulting in stacking faults which are manifested in anisotropic line broadening of their powder diffraction patterns. Analysis of a few commercial samples of adenine revealed them all to be a polymorph mixture, which could be inconvenient in experiments where properties of the solid material could be relevant.

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adenine_Manuscript_accepted.pdf - Accepted Manuscript
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Accepted/In Press date: 14 April 2016
e-pub ahead of print date: 14 April 2016
Published date: 26 April 2016
Organisations: Chemistry

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Local EPrints ID: 392739
URI: http://eprints.soton.ac.uk/id/eprint/392739
ISSN: 1528-7483
PURE UUID: d4b9a6a5-f2d5-4d47-ae1c-aa6c35f19972
ORCID for Graeme Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 15 Apr 2016 16:01
Last modified: 07 Oct 2020 04:40

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Contributors

Author: Tomislav Stolar
Author: Stipe Lukin
Author: Josip Pozar
Author: Mirta Rubcic
Author: Graeme Day ORCID iD
Author: Ivana Biljan
Author: Dubravka Sisak Jung
Author: Gordan Horvat
Author: Krunoslav Uzarevic
Author: Ernest Mestrovic
Author: Ivan Halasz

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