Posts Tagged ‘antiaromaticity’
Thursday, January 3rd, 2019
There is emerging interest in cyclic conjugated molecules that happen to have triplet spin states and which might be expected to follow a 4n rule for aromaticity.[1] The simplest such system would be the triplet state of cyclobutadiene, for which a non or anti-aromatic singlet state is always found to be lower in energy. Here I explore some crystal structures containing this motif for possible insights.
(more…)
References
-
A. Kostenko, B. Tumanskii, Y. Kobayashi, M. Nakamoto, A. Sekiguchi, and Y. Apeloig, "Spectroscopic Observation of the Triplet Diradical State of a Cyclobutadiene", Angewandte Chemie International Edition, vol. 56, pp. 10183-10187, 2017. http://dx.doi.org/10.1002/anie.201705228
Tags:antiaromaticity, aromaticity, Baird's rule, Conjugated system, crystal structure search, energy, Hückel's rule, Interesting chemistry, Nature, Physical organic chemistry, Physical sciences, search query, Triplet state
Posted in Uncategorised | No Comments »
Sunday, March 12th, 2017
This is another of those posts that has morphed from an earlier one noting the death of the great chemist George Olah. The discussion about the norbornyl cation concentrated on whether this species existed in a single minimum symmetric energy well (the non-classical Winstein/Olah proposal) or a double minimum well connected by a symmetric transition state (the classical Brown proposal). In a comment on the post, I added other examples in chemistry of single/double minima, mapped here to non-classical/classical structures. I now expand on the examples related to small aromatic or anti-aromatic rings.
(more…)
Tags:antiaromaticity, aromaticity, Évariste Galois, Carbocation, Chemistry, equilibrium minimum energy position, George Andrew Olah, George Olah, great chemist, Interesting chemistry, Jahn-Teller, minimum symmetric energy, Olah, Physical organic chemistry, Saul Winstein, symmetric energy potentials
Posted in Uncategorised | No Comments »
Sunday, March 5th, 2017
Cyclobutadiene is one of those small iconic molecules, the transience and instability of which was explained theoretically long before it was actually detected in 1965.[1] Given that instability, I was intrigued as to how many crystal structures might have been reported for this ring system, along with the rather more stable congener cyclo-octatetraene. Here is what I found.
(more…)
References
-
L. Watts, J.D. Fitzpatrick, and R. Pettit, "Cyclobutadiene", Journal of the American Chemical Society, vol. 87, pp. 3253-3254, 1965. http://dx.doi.org/10.1021/ja01092a049
Tags:antiaromaticity, Chemistry, cyclobutadiene, Instability, Nature, Physical organic chemistry, Physics, search query
Posted in crystal_structure_mining | 4 Comments »
Saturday, June 11th, 2011
In a time when large (molecules) are considered beautiful (or the corollary that beauty must be big), it is good to reflect that small molecules may teach us something as well. Take ethane. Is there anything left which has not been said about it already? Well, consider the reaction below, in which two hydrogen atoms mutually hop from one carbon to the other.
(more…)
Tags:animation, antiaromaticity, cyclic electron systems, distorsion, dyotropic, pericyclic, Tutorial material
Posted in Uncategorised | 4 Comments »