Solvation of a chiral carboxylic acid: effects of hydrogen bonding on the IR and VCD spectra of α-methoxyphenylacetic acid

Literature Information

Publication Date 2017-06-12
DOI 10.1039/C7CP02049J
Impact Factor 3.676
Authors

Karoline Bünnemann, Christian Merten


View Original

Abstract

Strong hydrogen bonding to solvent molecules can significantly alter the IR and VCD spectra of a chiral solute. This can be particularly troublesome for the determination of absolute configurations, as all spatial configurations of solute–solvent clusters need to be considered explicitly in spectra calculations. With this contribution, we aim to derive general guidelines for the explicit solvation of carboxylic acids, and characterize the solute–solvent interactions of the model compound α-methoxyphenylacetic acid (MPAA) in organic solvents of different polarity. We show that, in the typical concentration range employed for VCD studies, MPAA prefers the formation of dimers in chloroform. In the other investigated solvents (acetonitrile, methanol, and dimethyl sulfoxide), hydrogen bonded solute–solvent clusters have to be considered explicitly for the spectral analysis. We discuss the origin of the solvent dependence of the VCD spectra of MPAA in detail, show which vibrational modes are most strongly affected, and that the spectral response correlates with the hydrogen bonding strength.

Related Literature

Dielectric studies of freezing behavior in porous materials: Water and methanol in activated carbon fibres

K. E. Gubbins, R. Radhakrishnan

2001-03-13 Paper

DOI: 10.1039/B009792F

The concepts of non-Gibbsian and non-Lewisian properties in chemical thermodynamics

João Carlos R. Reis, Michael J. Blandamer, Michael I. Davis, Gérard Douhéret

2001-03-16 Paper

DOI: 10.1039/B009512P

Synthesis and characterisation of chromium-substituted ETS-10

Andreas Philippou, Anabela Valente, João Rocha, Michael Anderson

2001-04-03 Paper

DOI: 10.1039/B006828O

Indirect standard electromotive force data for the H2|HCl|AgCl|Ag cell for methanol–watersolvents with low water content

Ian C. Hamilton, George J. Kakabadse, Sue Le Vent

2001-03-14 Paper

DOI: 10.1039/B009408K

Vapour phase hydrogenation of crotonaldehyde over magnesia-supported platinum–tin catalysts

Narcís Homs, Jordi Llorca, Pilar Ramírez de la Piscina, Francisco Rodríguez-Reinoso, Antonio Sepúlveda-Escribano, Joaquín Silvestre-Albero

2001-03-29 Paper

DOI: 10.1039/B100770J

Characterisation of cation exchange membrane in hydro-organic media by electrochemistry and Raman spectroscopy

Christophe Innocent, Patrice Huguet, Jean Luc Bribes, Gérald Pourcelly, Mostefa Kameche

2001-03-19 Paper

DOI: 10.1039/B008318F

Electron magnetic resonance study of stable radicals in irradiated D-fructose single crystals

Gauthier Vanhaelewyn, Philippe Lahorte, Frank De Proft, Wim Mondelaers, Paul Geerlings, Freddy Callens

2001-04-03 Paper

DOI: 10.1039/B008248L

You might also like

Compound Q&A

What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?

(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...

79066-03-8(3.beta.)-3-Hydroxy-...
Compound Q&A

What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?

5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...

89702-89-65-(aminomethyl)-2-me...
Compound Q&A

What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?

Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...

28981-13-7Thieno[2,3-c]pyridin...
Compound Q&A

Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?

1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...

1185311-28-71-[(6-Methoxy-3-pyri...
Compound Q&A

What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?

[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...

146404-58-2[(2E)-3-Phenyl-2-pro...
Compound Q&A

What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?

6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...

1620515-86-76-Bromo-7-methoxyqui...
Compound Q&A

What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?

This compound is primarily used in the pharmaceutical industry for the developme...

260550-89-8(2R)-1-(1-Benzofuran...
1228013-15-71-Ethyl-7-[2-methyl-...
Compound Q&A

Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?

Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...

1217500-78-1{5-(Acryloylamino)-2...
Compound Q&A

What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?

3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...

310881-48-23-(Piperidin-4-yloxy...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.