The story so far. Inspired by the report of the most polar neutral compound yet made, I suggested some candidates based on the azulene ring system that if made might be even more polar. This then led to considering a smaller π-analogue of azulene, m-benzyne. Here I ponder how a derivative of this molecule might be made, using computational profiling as one reality check.
Archive for the ‘Interesting chemistry’ Category
Forming a stabilized m-benzyne.
Friday, January 20th, 2017Braiding a molecular knot with eight crossings.
Friday, January 20th, 2017This is one of those posts of a molecule whose very structure is interesting enough to merit a picture and a 3D model. The study[1] reports a molecular knot with the remarkable number of eight crossings.
References
- J.J. Danon, A. Krüger, D.A. Leigh, J. Lemonnier, A.J. Stephens, I.J. Vitorica-Yrezabal, and S.L. Woltering, "Braiding a molecular knot with eight crossings", Science, vol. 355, pp. 159-162, 2017. https://doi.org/10.1126/science.aal1619
Ritonavir: a look at a famous example of conformational polymorphism.
Monday, January 2nd, 2017Here is an inside peek at another one of Derek Lowe’s 250 milestones in chemistry, the polymorphism of Ritonavir.[1] The story in a nutshell concerns one of a pharma company’s worst nightmares; a drug which has been successfully brought to market unexpectedly “changes” after a few years on market to a less effective form (or to use the drug term, formulation). This can happen via a phenomenon known as polymorphism, where the crystalline structure of a molecule can have more than one form.[2],[3],[4] In this case, form I was formulated into soluble tablets for oral intake. During later manufacturing, a new less-soluble form appeared and “within weeks this new polymorph began to appear throughout both the bulk drug and formulation areas“[1]
References
- J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter, and J. Morris, "Ritonavir: An Extraordinary Example of Conformational Polymorphism", Pharmaceutical Research, vol. 18, pp. 859-866, 2001. https://doi.org/10.1023/a:1011052932607
- J.D. Dunitz, and J. Bernstein, "Disappearing Polymorphs", Accounts of Chemical Research, vol. 28, pp. 193-200, 1995. https://doi.org/10.1021/ar00052a005
- D. Bučar, R.W. Lancaster, and J. Bernstein, "Disappearing Polymorphs Revisited", Angewandte Chemie International Edition, vol. 54, pp. 6972-6993, 2015. https://doi.org/10.1002/anie.201410356
- G.J.O. Beran, I.J. Sugden, C. Greenwell, D.H. Bowskill, C.C. Pantelides, and C.S. Adjiman, "How many more polymorphs of ROY remain undiscovered", Chemical Science, vol. 13, pp. 1288-1297, 2022. https://doi.org/10.1039/d1sc06074k
The dipole moments of highly polar molecules: glycine zwitterion.
Saturday, December 24th, 2016The previous posts produced discussion about the dipole moments of highly polar molecules. Here to produce some reference points for further discussion I look at the dipole moment of glycine, the classic zwitterion (an internal ion-pair).
Forking “The most polar neutral compound synthesized” into m-benzyne.
Wednesday, December 21st, 2016A project fork is defined (in computing) as creating a distinct and separate strand from an existing (coding) project. Here I apply the principle to the polar azulene 4 explored in an earlier post, taking m-benzyne as a lower homologue of azulene as my starting point.
Molecules of the year? The most polar neutral compound synthesized…
Sunday, December 18th, 2016This, the fourth candidate provided by C&EN for a vote for the molecule of the year as discussed here, lays claim to the World’s most polar neutral molecule (system 1 shown below).[1] Here I explore a strategy for extending that record.
References
- J. Wudarczyk, G. Papamokos, V. Margaritis, D. Schollmeyer, F. Hinkel, M. Baumgarten, G. Floudas, and K. Müllen, "Hexasubstituted Benzenes with Ultrastrong Dipole Moments", Angewandte Chemie International Edition, vol. 55, pp. 3220-3223, 2016. https://doi.org/10.1002/anie.201508249