Virtual cocrystal screening

Musumeci, Daniele; Hunter, Christopher A.; Prohens, Rafel; Scuderi, Serena; McCabe, James F.

doi:10.1039/c0sc00555j

Cited by 278 publications

(306 citation statements)

References 39 publications

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“…6 However, cyanooximes, 7 where the oxime nitrogen atom is a 25 particularly weak hydrogen-bond acceptor due to the presence of the electron-withdrawing -CN moiety, 8,9 tend to act as a single point hydrogen-bond donors similar to an -OH group. 10 The latter functionality is ubiquitous in biological systems, and is also heavily utilized in applications such as templated covalent 30 synthesis, 11 nonlinear optics 12 and sensors.…”

Section: Scheme 1 the Oxime Moietymentioning

confidence: 99%

Competing hydrogen-bond donors: phenols vs. cyanooximes

et al. 2013

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Section: Scheme 1 the Oxime Moietymentioning

confidence: 99%

Competing hydrogen-bond donors: phenols vs. cyanooximes

et al. 2013

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“…Many theoretical approaches were developed as suitable for this purpose, but among them those taking advantage of relatively inexpensive scans of potential cocrystallization propensities seem to be worth considering. For example, characteristics of the electrostatic potential surface of the interacting molecules can be used for identification of the most likely contacts [42]. A virtual cocrystal screening method [43] was successfully validated against experimental cocrystals.…”

Section: Introductionmentioning

confidence: 99%

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Cysewski

2016

Struct Chem

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New virtual cocrystal screening was proposed taking advantage of the similarities between cocrystallization landscapes of different compounds. Assuming that cocrystallization propensities can be modeled by miscibility affinities of liquid components under supercooled conditions, the quantitative rules of likeness were formulated and validated for 45 aromatic and heteroaromatic amides interacting with a variety of coformers. The most important finding comes from the observed linear trends between the values of mixing enthalpies of amides with respect to a reference molecule. Particularly isonicotinamide was found as a very convenient comparative system since it constitutes 97 binary cocrystals. Many experimentally observed cocrystals were used for supporting the analogy hypothesis, which states that a properly selected reference molecule, for which cocrystals were experimentally documented, can provide practical information about cocrystallization propensities of another compound provided that two criterions are met, namely sufficiently high similarities and high enough affinities. Hence, it is not necessary to perform experimental cocrystallization of every pair of coformers since miscibility in the solid state of one compound can be transferred to another one at least in the case of aromatic or heteroaromatic amides.

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“…Musumeci et al predicted that all the possible intermolecular interaction sites present on the surface of molecules were responsible for the formation of cocrystals [71] . The strength of hydrogen bond depends upon the H-bond donors and H-bond acceptors; best H-bond donor and best H-bond form the strongest H-bond, and next best H-bond acceptor interacted with the next H-bond donor, and so on, until all sites are satisfied.…”

Section: Virtual Cocrystal Screeningmentioning

confidence: 99%

“…The results showed that the probability of cocrystal formation was 50% more, when ∆E difference of cocrystals and two pure solids should be more than 11 kJ/mol. This approach was validated by using about 1000 compounds from literature for APIs (caffeine and carbamazepine) and ∆E parameter was found to be favourable and fast screening tool [71] .…”

Section: Virtual Cocrystal Screeningmentioning

confidence: 99%