First Principles Simulations of Optical Rotation of Chiral Molecular Crystals.

chiral crystals density functional theory optical rotation periodic boundary conditions

Journal

Chirality

ISSN: 1520-636X

Titre abrégé: Chirality

Pays: United States

ID NLM: 8914261

Informations de publication

Date de publication:
Aug 2024

Historique:

revised: 12 07 2024

received: 11 06 2024

accepted: 15 07 2024

medline: 5 8 2024

pubmed: 5 8 2024

entrez: 5 8 2024

Statut: ppublish

Résumé

In this work, we present simulations of the optical rotation (OR) for five molecular crystals at density functional theory level with periodic boundary conditions (DFT-PBC). Calculations are compared with experimental measurements and show semi-quantitative agreement with experimental data for three of the crystals: tartatic acid, benzil, and pentaerythritol. For the other two crystals, aspartic acid and glutamic acid, the calculated data are in qualitative agreement with, but two orders of magnitude smaller than, the experimental data. We provide some arguments that support the theoretical predictions and suggest that the experiments should be revisited. We also find that the position of H centers provided in experimental X-ray data is not sufficiently reliable for simulating OR, and better results are obtained when H atoms are allowed to relax while keeping heavier elements fixed at the experimental positions. Comparison with molecular cluster calculations with a better functional and a larger basis set indicate that the role of intermolecular interactions (reproduced with the PBC technique) is as or more important than the choice of model chemistry. Despite the current limitations in the level of theory that can be employed, these simulations provide a promising avenue to investigate the effect of intermolecular interactions on this sensitive electronic property of molecules and materials.

Identifiants

DOI: 10.1002/chir.23709 PMID: 39101242

pubmed: 39101242

doi: 10.1002/chir.23709

doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

Pagination

e23709

Subventions

Organisme : National Science Foundation

ID : CHE-2154452

Organisme : NSF

ID : MRI-2117449

Informations de copyright

Références

L. D. Barron, Molecular Light Scattering Optical Activity 2nd ed., (Cambridge University Press, 2004).

J.‐B. Biot, Mémoire sur un nouveau genre d'oscillation que les molécules de la lumière éprouvent en traversant certains cristaux (Chez Firmin Didot, 1814).

B. Kahr and O. Arteaga, “Arago's Best Paper,” ChemPhysChem 13, no. 1 (2012): 79–88.

N. Berova, P. L. Polavarapu, K. Nakanishi, and R. W. Woody, eds., Comprehensive Chiroptical Spectroscopy: Instrumentation, Methodologies, and Theoretical Simulations 1st ed., (Wiley, 2011), https://onlinelibrary.wiley.com/doi/book/10.1002/9781118120187.

D. W. Urry, “Optical Rotation,” Annual Review of Physical Chemistry 19, no. 1 (1968): 477–530. https://www.annualreviews.org/doi/10.1146/annurev.pc.19.100168.002401.

T. Müller, K. B. Wiberg, and P. H. Vaccaro, “Cavity Ring‐Down Polarimetry (CRDP): A New Scheme for Probing Circular Birefringence and Circular Dichroism in the Gas Phase,” Journal of Physical Chemistry A 104, no. 25 (2000): 5959–5968. https://pubs.acs.org/doi/10.1021/jp000705n.

T. Müller, K. B. Wiberg, P. H. Vaccaro, J. R. Cheeseman, and M. J. Frisch, “Cavity Ring‐Down Polarimetry (CRDP): Theoretical and Experimental Characterization,” Journal of the Optical Society of America B 19, no. 1 (2002): 125. https://opg.optica.org/abstract.cfm?URI=josab‐19‐1‐125.

K. Claborn, J. Herreros Cedres, C. Isborn, et al., “Optical Rotation of Achiral Pentaerythritol,” Journal of the American Chemical Society 128, no. 46 (2006): 14746–14747. https://pubs.acs.org/doi/10.1021/ja064631q.

K. Claborn, C. Isborn, W. Kaminsky, and B. Kahr, “Optical Rotation of Achiral Compounds,” Angewandte Chemie International Edition 47, no. 31 (2008): 5706–5717. https://onlinelibrary.wiley.com/doi/10.1002/anie.200704559.

J. Autschbach, “Computing Chiroptical Properties With First‐Principles Theoretical Methods: Background and Illustrative Examples,” Chirality 21, no. 1E (2009): E116–E152. https://onlinelibrary.wiley.com/doi/10.1002/chir.20789.

J. Autschbach, “Time‐Dependent Density Functional Theory for Calculating Origin–Independent Optical Rotation and Rotatory Strength Tensors,” ChemPhysChem 12, no. 17 (2011): 3224–3235. https://chemistry‐europe.onlinelibrary.wiley.com/doi/10.1002/cphc.201100225.

J. R. Cheeseman, M. J. Frisch, F. J. Devlin, and P. J. Stephens, “Hartree‐Fock and Density Functional Theory Ab Initio Calculation of Optical Rotation Using GIAOs: Basis Set Dependence,” Journal of Physical Chemistry A 104, no. 5 (2000): 1039–1046.

T. D. Crawford, “Ab Initio Calculation of Molecular Chiroptical Properties,” Theoretical Chemistry Accounts 115, no. 4 (2006): 227–245. http://link.springer.com/10.1007/s00214‐005‐0001‐4.

T. D. Crawford and P. J. Stephens, “Comparison of Time‐Dependent Density‐Functional Theory and Coupled Cluster Theory for the Calculation of the Optical Rotations of Chiral Molecules,” Journal of Physical Chemistry A 112, no. 6 (2008): 1339–1345.

M. Krykunov and J. Autschbach, “Calculation of Optical Rotation With Time‐Periodic Magnetic‐Field‐Dependent Basis Functions in Approximate Time‐Dependent Density‐Functional Theory,” Journal of Chemical Physics 123, no. 11 (2005): 114103. https://pubs.aip.org/jcp/article/123/11/114103/186995/Calculation‐of‐optical‐rotation‐with‐time‐periodic.

M. Krykunov and J. Autschbach, “Calculation of Origin‐Independent Optical Rotation Tensor Components in Approximate Time‐Dependent Density Functional Theory,” Journal of Chemical Physics 125, no. 3 (2006): 34102. https://pubs.aip.org/jcp/article/125/3/034102/564398/Calculation‐of‐origin‐independent‐optical‐rotation.

P. Norman, K. Ruud, and T. Helgaker, “Density‐Functional Theory Calculations of Optical Rotatory Dispersion in the Nonresonant and Resonant Frequency Regions,” Journal of Chemical Physics 120, no. 11 (2004): 5027–5035.

T. Parsons, T. Balduf, J. R. Cheeseman, and M. Caricato, “Basis Set Dependence of Optical Rotation Calculations With Different Choices of Gauge,” Journal of Physical Chemistry A 126, no. 11 (2022): 1861–1870. https://pubs.acs.org/doi/10.1021/acs.jpca.2c00201.

P. L. Polavarapu, “Ab Initio Molecular Optical Rotations and Absolute Configurations,” Molecular Physics 91, no. 3 (1997): 551–554.

P. L. Polavarapu, D. K. Chakraborty, and K. Ruud, “Molecular Optical Rotation: An Evaluation of Semiempirical Models,” Chemical Physics Letters 319, no. 5 (2000): 595–600.

P. L. Polavarapu, “Optical Rotation: Recent Advances in Determining the Absolute Configuration,” Chirality 14, no. 10 (2002): 768–781.

K. Ruud and T. Helgaker, “Optical Rotation Studied by Density‐Functional and Coupled‐Cluster Methods,” Chemical Physics Letters 352, no. 5‐6 (2002): 533–539.

K. Ruud, P. J. Stephens, F. J. Devlin, P. R. Taylor, J. R. Cheeseman, and M. J. Frisch, “Coupled‐Cluster Calculations of Optical Rotation,” Chemical Physics Letters 373, no. 5‐6 (2003): 606–614.

M. Srebro, N. Govind, W. A. de Jong, and J. Autschbach, “Optical Rotation Calculated With Time‐Dependent Density Functional Theory: The OR45 Benchmark,” Journal of Physical Chemistry A 115, no. 40 (2011): 10930–10949.

P. J. Stephens, F. J. Devlin, J. R. Cheeseman, and M. J. Frisch, “Calculation of Optical Rotation Using Density Functional Theory,” Journal of Physical Chemistry A 105, no. 22 (2001): 5356–5371.

P. J. Stephens, F. J. Devlin, J. R. Cheeseman, M. J. Frisch, and C. Rosini, “Determination of Absolute Configuration Using Optical Rotation Calculated Using Density Functional Theory,” Organic Letters 4, no. 26 (2002): 4595–4598. https://pubs.acs.org/doi/10.1021/ol0201714.

P. Lahiri, K. B. Wiberg, and P. H. Vaccaro, “Intrinsic Optical Activity and Large‐Amplitude Displacement: Conformational Flexibility in (R)‐Glycidyl Methyl Ether,” Journal of Physical Chemistry A 119, no. 30 (2015): 8311–8327. https://pubs.acs.org/doi/10.1021/acs.jpca.5b05177.

P. Lahiri, K. B. Wiberg, P. H. Vaccaro, M. Caricato, and T. D. Crawford, “Large Solvation Effect in the Optical Rotatory Dispersion of Norbornenone,” Angewandte Chemie International Edition 126, no. 5 (2014): 1410–1413. https://onlinelibrary.wiley.com/doi/10.1002/ange.201306339.

P. H. Vaccaro, Comprehensive Chiroptical Spectroscopy, Instrumentation, Methodologies, and Theoretical Simulations 1st ed., (New York: John Wiley & Sons, 2012).

T. Aharon, P. Lemler, P. H. Vaccaro, and M. Caricato, “Comparison of Measured and Predicted Specific Optical Rotation in Gas and Solution phases: A Test for the Polarizable Continuum Model of Solvation,” Chirality 30, no. 4 (2018): 383–395.

T. D. Crawford, A. Kumar, K. P. Hannon, S. Höfener, and L. Visscher, “Frozen‐Density Embedding Potentials and Chiroptical Properties,” Journal of Chemical Theory and Computation 11, no. 11 (2015): 5305–5315.

R. D'Cunha and T. D. Crawford, “Modeling Complex Solvent Effects on the Optical Rotation of Chiral Molecules: A Combined Molecular Dynamics and Density Functional Theory Study,” Journal of Physical Chemistry A 125, no. 15 (2021): 3095–3108.

F. Egidi, T. Giovannini, G. Del Frate, P. M. Lemler, P. H. Vaccaro, and C. Cappelli, “A Combined Experimental and Theoretical Study of Optical Rotatory Dispersion for (R)‐Glycidyl Methyl Ether in Aqueous Solution,” Physical Chemistry Chemical Physics 21 (2019): 3644–3655. https://doi.org/10.1039/C8CP04445G.

M. D. Kundrat and J. Autschbach, “Ab Initio and Density Functional Theory Modeling of the Chiroptical Response of Glycine and Alanine in Solution Using Explicit Solvation and Molecular Dynamics,” Journal of Chemical Theory and Computation 4, no. 11 (2008): 1902–1914.

M. D. Kundrat and J. Autschbach, “Modeling of the Chiroptical Response of Chiral Amino Acids in Solution Using Explicit Solvation and Molecular Dynamics,” Journal of Chemical Theory and Computation 5, no. 4 (2009): 1051–1060.

B. Mennucci, C. Cappelli, R. Cammi, and J. Tomasi, “Modeling Solvent Effects on Chiroptical Properties,” Chirality 23, no. 9 (2011): 717–729.

P. Mukhopadhyay, G. Zuber, M.‐R. Goldsmith, P. Wipf, and D. N. Beratan, “Solvent Effect on Optical Rotation: A Case Study of Methyloxirane in Water,” ChemPhysChem 7, no. 12 (2006): 2483–2486.

P. Mukhopadhyay, G. Zuber, P. Wipf, and D. N. Beratan, “Contribution of a Solute's Chiral Solvent Imprint to Optical Rotation,” Angewandte Chemie International Edition 46, no. 34 (2007): 6450–6452.

P. Lahiri, K. B. Wiberg, and P. H. Vaccaro, “A Tale of Two Carenes: Intrinsic Optical Activity and Large‐Amplitude Nuclear Displacement,” Journal of Physical Chemistry A 116, no. 38 (2012): 9516–9533. https://pubs.acs.org/doi/10.1021/jp303270d.

T. Asahi, M. Takahashi, and J. Kobayashi, “The Optical Activity of Crystalline L ‐Aspartic Acid,” Acta Crystallographica Section A: Foundations of Crystallography 53, no. 6 (1997): 763–771. https://scripts.iucr.org/cgi‐bin/paper?S0108767397004595.

T. Asahi, H. Utsumi, Y. Itagaki, I. Kagomiya, and J. Kobayashi, “Optical Activity of Crystalline Glutamic Acids,” Acta Crystallographica Section A: Foundations of Crystallography 52, no. 5 (1996): 766–769. https://scripts.iucr.org/cgi‐bin/paper?S010876739609993X.

J. Freudenthal, W. Kaminsky, and B. Kahr, “Chiroptical Imaging of Crystals,” in Comprehensive Chiroptical Spectroscopy, eds. N. Berova, P. L. Polavarapu, K. Nakanishi, and R. W. Woody (Hoboken, New Jersey: Wiley, 2012), 325–345.

B. Kahr, J. Freudenthal, and E. Gunn, “Crystals in Light,” Accounts of Chemical Research 43, no. 5 (2010): 684–692.

W. Kaminsky, K. Claborn, and B. Kahr, “Polarimetric Imaging of Crystals,” Chemical Society Review 33, no. 8 (2004): 514.

D. Mucha, K. Stadnicka, W. Kaminsky, and A. M. Glazer, “Determination of Optical Activity in Monoclinic Crystals of Tartaric Acid, Using the ‘Tilter’ Method,” Journal of Physics Condensed Matter 9, no. 49 (1997): 10829–10842. https://iopscience.iop.org/article/10.1088/0953‐8984/9/49/004.

K. Nakagawa, A. T. Martin, S. M. Nichols, V. L. Murphy, B. Kahr, and T. Asahi, “Optical Activity Anisotropy of Benzil,” Journal of Physical Chemistry C 121, no. 45 (2017): 25494–25502. https://pubs.acs.org/doi/10.1021/acs.jpcc.7b08831.

J. H. Freudenthal, E. Hollis, and B. Kahr, “Imaging Chiroptical Artifacts,” Chirality 21, no. 1E (2009): E20–E27. https://onlinelibrary.wiley.com/doi/10.1002/chir.20768.

T. Balduf and M. Caricato, “Derivation and Implementation of the Optical Rotation Tensor for Chiral Crystals,” Journal of Chemical Physics 157, no. 21 (2022): 214105. https://pubs.aip.org/jcp/article/157/21/214105/2842077/Derivation‐and‐implementation‐of‐the‐optical.

M. Caricato, “A Perspective on the Simulation of Electronic Circular Dichroism and Circularly Polarized Luminescence Spectra in Chiral Solid Materials,” Journal of Physical Chemistry A 128, no. 7 (2024): 1197–1206.

J. K. Desmarais, B. Kirtman, and M. Rérat, “First‐Principles Calculation of the Optical Rotatory Power of Periodic Systems: Modern Theory With Modern Functionals,” Physical Review B 107 (2023): 224430. https://link.aps.org/doi/10.1103/PhysRevB.107.224430.

M. Rérat and B. Kirtman, “First‐Principles Calculation of the Optical Rotatory Power of Periodic Systems: Application on α$$ \alpha $$‐Quartz, Tartaric Acid Crystal, and Chiral (n,m)‐Carbon Nanotubes,” Journal of Chemical Theory and Computation 17, no. 7 (2021): 4063–4076.

X. Wang and Y. Yan, “Optical Activity of Solids From First Principles,” Physical Review B 107 (2023): 45201. https://link.aps.org/doi/10.1103/PhysRevB.107.045201.

A. D. Buckingham and M. B. Dunn, “Optical Activity of Oriented Molecules,” Journal of the Chemical Society A: Inorganic, Physical, Theoretical (1971): 1988–1991. https://xlink.rsc.org/?DOI=j19710001988.

O. Christiansen, P. Jørgensen, and C. Hättig, “Response Functions From Fourier Component Variational Perturbation Theory Applied to a Time‐Averaged Quasienergy,” International Journal of Quantum Chemistry 68, no. 1 (1998): 1–52. https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1097‐461X(1998)68:1<1::AID‐QUA1>3.0.CO;2‐Z.

H. Koch and P. Jørgensen, “Coupled Cluster Response Functions,” Journal of Chemical Physics 93, no. 5 (1990): 3333–3344. https://pubs.aip.org/jcp/article/93/5/3333/971836/Coupled‐cluster‐response‐functionsCoupled‐cluster.

T. Helgaker, K. Ruud, K. L. Bak, P. Jørgensen, and J. Olsen, “Vibrational Raman Optical Activity Calculations Using London Atomic Orbitals,” Faraday Discussions 99 (1994): 165–180.

F. London, “Théorie quantique des courants interatomiques dans les combinaisons aromatiques,” Journal de Physique et Le Radium 8, no. 10 (1937): 397–409.

M. Caricato, “Origin Invariant Optical Rotation in the Length Dipole Gauge Without London Atomic Orbitals,” Journal of Chemical Physics 153, no. 15 (2020): 151101.

M. Caricato and T. Balduf, “Origin Invariant Full Optical Rotation Tensor in the Length Dipole Gauge Without London Atomic Orbitals,” Journal of Chemical Physics 155, no. 2 (2021): 24118. https://pubs.aip.org/jcp/article/155/2/024118/1065026/Origin‐invariant‐full‐optical‐rotation‐tensor‐in.

T. B. Pedersen, H. Koch, L. Boman, and A. M. J. Sánchez De Merás, “Origin Invariant Calculation of Optical Rotation Without Recourse to London Orbitals,” Chemical Physics Letters 393, no. 4‐6 (2004): 319–326. https://linkinghub.elsevier.com/retrieve/pii/S0009261404009339.

K. Zhang, T. Balduf, and M. Caricato, “Full Optical Rotation Tensor at Coupled Cluster With Single and Double Excitations Level in the Modified Velocity Gauge,” Chirality 33, no. 6 (2021): 303–314.

J. F. Nye, Physical Properties of Crystals: Their Representation by Tensors and Matrices Oxford Science Publications (Clarendon Press, 1985).

J. Heyd, J. E. Peralta, G. E. Scuseria, and R. L. Martin, “Energy Band Gaps and Lattice Parameters Evaluated With the Heyd‐Scuseria‐Ernzerhof Screened Hybrid Functional,” Journal of Chemical Physics 123, no. 17 (2005): 174101. https://pubs.aip.org/jcp/article/123/17/174101/917481/Energy‐band‐gaps‐and‐lattice‐parameters‐evaluated.

V. A. Rassolov, M. A. Ratner, J. A. Pople, P. C. Redfern, and L. A. Curtiss, “6–31G* Basis Set for Third‐Row Atoms,” Journal of Computational Chemistry 22, no. 9 (2001): 976–984. https://onlinelibrary.wiley.com/doi/10.1002/jcc.1058.

T. Yanai, D. P. Tew, and N. C. Handy, “A New Hybrid Exchange–Correlation Functional Using the Coulomb‐Attenuating Method (CAM‐B3LYP),” Chemical Physics Letters 393, no. 1‐3 (2004): 51–57. https://linkinghub.elsevier.com/retrieve/pii/S0009261404008620.

T. H. Dunning, “A Road Map for the Calculation of Molecular Binding Energies,” Journal of Physical Chemistry A 104, no. 40 (2000): 9062–9080. https://pubs.acs.org/doi/10.1021/jp001507z.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian Development Version Revision j. 06+ (Wallingford CT: Gaussian Inc., 2020).

J. Drenth and J. Mesters, Principles of Protein X‐Ray Crystallography 3rd ed., (New York: Springer, 2007).

C. Adamo and V. Barone, “Toward Reliable Density Functional methods Without Adjustable Parameters: The PBE0 Model,” Journal of Chemical Physics 110, no. 13 (1999): 6158–6170. https://doi.org/10.1063/1.478522.

L. I. Katzin and E. Gulyas, “Optical Rotatory Dispersion of Some Amino Acids and Criteria of Protein Conformation,” Journal of the American Chemical Society 86, no. 9 (1964): 1655–1659. https://pubs.acs.org/doi/abs/10.1021/ja01063a001.

B. C. Mort and J. Autschbach, “Magnitude of Zero‐Point Vibrational Corrections to Optical Rotation in Rigid Organic Molecules: A Time‐Dependent Density Functional Study,” Journal of Physical Chemistry A 109, no. 38 (2005): 8617–8623. https://doi.org/10.1021/jp051685y.

B. C. Mort and J. Autschbach, “Temperature Dependence of the Optical Rotation of Fenchone Calculated by Vibrational Averaging,” Journal of Physical Chemistry A 110, no. 40 (2006): 11381–11383.

H.‐M. Ye, J. Xu, J. Freudenthal, and B. Kahr, “On the Circular Birefringence of Polycrystalline Polymers: Polylactide,” Journal of the American Chemical Society 133, no. 35 (2011): 13848–13851.