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VCD Chirality Transfer: A New Insight into the Intermolecular Interactions

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Practical Aspects of Computational Chemistry I

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Abstract

The Vibrational Circular Dichroism (VCD) spectroscopy has been developing rapidly in both experimental and theoretical aspects. Currently, the VCD has become one of the most effective and reliable spectroscopic technique to determine the absolute configuration of chiral molecules. Its success is related to the availability of instrumentation and software for quantum-chemical calculation of the spectra. Nowadays, large parts of the VCD spectra can be trustfully predicted by theory and critically verified by confiding experiment, and vice versa. In the last decade, several theoretical and experimental VCD studies reported on VCD chirality transfer phenomenon occurring when an achiral molecule becomes VCD active as a result of intermolecular interactions with a chiral one. There are still some theoretical and experimental uncertainties about the VCD chirality transfer, however, benefits from an comprehensive use of the phenomenon can push our ability to diversify the intermolecular complexes and deepen our understanding of intermolecular interactions. This chapter is a review of the computational studies on VCD chirality transfer phenomenon supported by the experimental references, and ended by perspectives.

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Notes

  1. 1.

    “Je montre, en effet, que l’hémiédrie est liée avec le sens de la polarisation rotatoire. Or, ce dernier phénomène étant moléculaire et accusant une dissymétrie dans les molécules, l’hémiédrie, à son tour, se trouve donc en étroite connexion avec la dissymétrie des derniers éléments qui composent le cristal.”

  2. 2.

    “Was kann wohl meiner Hand oder meinem Ohr ähnlicher, und in allen Stücken gleicher sein, als ihr Bild im Spiegel? Und dennoch kann ich eine solche Hand, als im Spiegel gesehen wird, nicht an die Stelle ihres Urbildes setzen; denn wenn dieses eine rechte Hand war, so ist jene im Spiegel eine linke, und das Bild des rechten Ohres ist ein linkes, das nimmermehr die Stelle des ersteren vertreten kann. Nun sind hier keine innre Unterschiede, die irgendein Verstand nur denken könnte; und dennoch sind die Unterschiede innerlich, soweit die Sinne lehren, denn die linke Hand kann mit der rechten, ohnerachtet aller beiderseitigen Gleichheit und Ähnlichkeit, doch nicht zwischen denselben Grenzen eingeschlossen sein, (sie können nicht kongruieren) der Handschuh der einen Hand kann nicht auf der andern gebraucht werden. Was ist nun die Auflösung? Diese Gegenstände sind nicht etwa Vorstellungen der Dinge, wie sie an sich selbst sind, und wie sie der pure Verstand erkennen würde, sondern es sind sinnliche Anschauungen, d. i. Erscheinungen, deren Möglichkeit auf dem Verhältnisse gewisser an sich unbekannten Dinge zu etwas anderem, nämlich unserer Sinnlichkeit beruht. Von dieser ist nun der Raum die Form der äußern Anschauung, und die innere Bestimmung eines jeden Raumes ist nur durch die Bestimmung des äußeren Verhältnisses zu dem ganzen Raume, davon jener ein Teil ist, (dem Verhältnisse zum äußeren Sinne) d. i. der Teil ist nur durchs Ganze möglich, welches bei Dingen an sich selbst, als Gegenständen des bloßen Verstandes niemals, wohl aber bei bloßen Erscheinungen stattfindet. Wir können daher auch den Unterschied ähnlicher und gleicher, aber doch inkongruenter Dinge (z. B. widersinnig gewundener Schnecken) durch keinen einzigen Begriff verständlich machen, sondern nur durch das Verhältnis zur rechten und linken Hand, welches unmittelbar auf Anschauung geht.”

    “What can be more similar in every respect and in every part more alike to my hand and to my ear, than their images in a mirror? And yet I cannot put such a hand as is seen in the glass in the place of its archetype; for if this is a right hand, that in the glass is a left one, and the image or reflection of the right ear is a left one which never can serve as a substitute for the other. There are in this case no internal differences which our understanding could determine by thinking alone. Yet the differences are internal as the senses teach, for, notwithstanding their complete equality and similarity, the left hand cannot be enclosed in the same bounds as the right one (they are not congruent); the glove of one hand cannot be used for the other. What is the solution? These objects are not representations of things as they are in themselves, and as the pure understanding would know them, but sensuous intuitions, that is, appearances, the possibility of which rests upon the relation of certain things unknown in themselves to something else, viz., to our sensibility. Space is the form of the external intuition of this sensibility, and the internal determination of every space is only possible by the determination of its external relation to the whole space, of which it is a part (in other words, by its relation to the external sense). That is to say, the part is only possible through the whole, which is never the case with things in themselves, as objects of the mere understanding, but with appearances only. Hence the difference between similar and equal things, which are yet not congruent(for instance, two symmetric helices), cannot be made intelligible by any concept, but only by the relation to the right and the left hands which immediately refers to intuition.”

  3. 3.

    3“Other members of this same school say there are ten principles, which they arrange in two columns of cognates-limit and unlimited, odd and even, one and plurality, right and left, male and female, resting and moving, straight and curved, light and darkness, good and bad, square and oblong. In this way Alcmaeon of Croton seems also to have conceived the matter, and either he got this view from them or they got it from him; for he expressed himself similarly to them. For he says most human affairs go in pairs, meaning not definite contrarieties such as the Pythagoreans speak of, but any chance contrarieties, e.g. white and black, sweet and bitter, good and bad, great and small. He threw out indefinite suggestions about the other contrarieties, but the Pythagoreans declared both how many and which their contraricties are.”

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Acknowledgments

This work was supported by Ministry of Science and Higher Education in Poland Grants No. NN204 242034 and N N204 443140. The computational Grants G19–4 and G31–13 from the Interdisciplinary Center of Mathematical and Computer Modeling (ICM) at the University of Warsaw are gratefully acknowledged.

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  1. National Medicines Institute, 30/34 Chełmska Street, 00-725, Warsaw, Poland

    Jan Cz. Dobrowolski & Joanna Sadlej

  2. Industrial Chemistry Research Institute, 8 Rydygiera Street, 01-793, Warsaw, Poland

    Jan Cz. Dobrowolski & Joanna E. Rode

  3. Faculty of Chemistry, University of Warsaw, 1 Pasteura Street, 02-093, Warsaw, Poland

    Joanna Sadlej

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  1. Jan Cz. Dobrowolski
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  1. Department of Chemistry, Jackson State University, 17910, P.O. Box 17910, 1400 Lynch St., Jackson, 39217, Mississippi, USA

    Jerzy Leszczynski

  2. Dept. Chemistry, Jackson State University, J. R. Lynch St. 1325, Jackson, 39217, Mississippi, USA

    Manoj K. K. Shukla

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Dobrowolski, J.C., Rode, J.E., Sadlej, J. (2011). VCD Chirality Transfer: A New Insight into the Intermolecular Interactions. In: Leszczynski, J., Shukla, M.K. (eds) Practical Aspects of Computational Chemistry I. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0919-5_15

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