ADVERTISEMENT

Investigating The Connectivity Between Atoms In Chiral Molecules

When the mirror image of the structure of a molecule cannot be superimposed on its parent structure, these two molecules with non-superimposable chemical structures are called enantiomers and the corresponding compounds fall under the category of chiral compounds. The enantiomers have opposite handedness, loosely categorized as left handed and right handed. Even though the enantiomers with non-superimposable mirror image structures have the same chemical composition, their chemical properties can be drastically different.

Human life owes much of its existence to chirality because the life-controlling proteins in the human body are made of chiral amino acids, all with one particular handedness. Because of this specificity of handedness in our human body, it is necessary to have the proper handedness for a chiral drug compound to function beneficially, when ingested. Therefore, it is of utmost importance to properly characterize, and document, the handedness of chiral compounds used for treating the human illnesses. In this characterization process, establishing the correct chemical structure of chiral molecules is the first step.

ADVERTISEMENT

If an error occurs in this first step, all subsequent analyses would lose relevance. Continuous ongoing developments in scientific methods are providing sophisticated methods for verifying the chemical structures of chiral compounds.

Among the latest methods are Raman optical activity (ROA) and vibrational circular dichroism (VCD), which along with two other methods, electronic circular dichroism (ECD) and optical rotatory dispersion (ORD), are categorized as the branches of chiroptical spectroscopy. In this paper, we propose a new application of chiroptical spectroscopy.

ROA and VCD methods have come into existence in the early 1970s and since then blossomed into practically useful methods for establishing the handedness of chiral compounds. These methods depend on the fact a molecule with a particular handedness will interact differently with left handed and right handed light waves, also referred to as left circularly polarized (LCP) light and right circularly polarized (RCP) light waves.

ROA and VCD spectroscopies derive their usefulness from the differences in the interaction of LCP and RCP light waves with the vibrational transitions of a chiral molecule, and these differences depend on the chemical structure of that molecule.

ADVERTISEMENT

ROA and VCD spectroscopies have recently been used to establish the absolute configurations (ACs), for the first time, of chiral molecules, isoflurane, bromochlorofluoromethane, and neopentane-d6. They were also used to confirm the known ACs of several chiral molecules. In all reported applications of chiroptical spectroscopy, the connectivities between the atoms of the studied chiral molecule were known.

If the connectivities between the atoms in a given chiral molecule are not known with certainty, then can chiroptical spectroscopic methods distinguish between the correct and incorrect atomic connectivities? To answer this question, several chiral compounds whose chemical structures have been mis-assigned in the literature, and later corrected, were subjected to chiroptical spectroscopic investigations.

Using spectral similarity overlap criteria, it was found that ROA and VCD spectroscopies, when applied carefully, can discriminate between the correct and incorrect atomic connectivities in chiral molecular structures. This observation is the basis for a new approach for identifying the incorrect chemical structures of chiral compounds.

This study, “To Avoid Chasing Incorrect Chemical Structures of Chiral Compounds: Raman Optical Activity and Vibrational Circular Dichroism Spectroscopies” was recently published (ChemPhysChem 2017, 18, 2459–2465). For more detailed information please see “Chiroptical Spectroscopy: Fundamentals and Applications”, Prasad L. Polavarapu, Taylor & Francis (2017).

ADVERTISEMENT

Comments

READ THIS NEXT

Archaebacteria: Definition And Examples

Archaebacteria are similar in form to bacteria, but they are different from the normal bacteria that biologists often study. In […]

Phosphorus Recovery – A Voyage From Sewage Sludge To Johannes Vermeer

What is phosphorus recovery about? Phosphorus as a nutrient – importance for our society ADVERTISEMENT Phosphorus is a chemical element. […]

Welcome To Your Autonomous Life: Self Driving Cars Are A New Reality

Autonomous vehicles have become a hot topic among professionals in both automotive and technology fields. Recent headlines have consumers dreaming […]

Bhutan’s Forest Conservation Policies Effectively Influence Forest Cover Changes

Although tropical deforestation is still widespread, reforestation is observed in several tropical countries, mostly in marginal lands including mountain environments. […]

Photophobia And Magnetism: First Date For An Interesting Liaison

Photophobia describes an experience of discomfort or pain in response to light conditions. In normal conditions, it can be provoked […]

Why Autoimmunity?

Autoimmunity is defined as occurring when the body’s immune system attacks healthy cells of a given organ. Given the process […]

How Environmental Moisture Influences Scratch Resistance Of Polymers

Polymeric materials are replacing metals and ceramics in the manufacturing of a wide range of products owing to their low […]

Science Trends is a popular source of science news and education around the world. We cover everything from solar power cell technology to climate change to cancer research. We help hundreds of thousands of people every month learn about the world we live in and the latest scientific breakthroughs. Want to know more?