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Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Chirality

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Radical Halogenation: Stereochemistry

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

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An Electrochemical Cholesteric Liquid Crystalline Device for Quick and Low-Voltage Color Modulation

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Salto de cristal direccional controlado por la quiralidad

Yifu Chen¹, Jiaxing Zhang², Jie Zhang¹

¹Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China.

Journal of the American Chemical Society

|March 13, 2024

Resumen

Este resumen es generado por máquina.

Los cristales quirales del monohidrato de asparagina muestran un salto direccional cuando se calientan, lo que demuestra la quiralidad molecular

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Área de la Ciencia:

La cristalografía
Ciencias de los materiales
Física Química

Sus antecedentes:

La quiralidad molecular es fundamental para los sistemas químicos y biológicos.
Comprender las consecuencias macroscópicas de la quiralidad molecular es un desafío científico continuo.

Objetivo del estudio:

Investigar el papel de la quiralidad molecular en la dirección del movimiento macroscópico del cristal.
Explorar el potencial de la dinámica de los cristales quirales para aplicaciones como la resolución quiral.

Principales métodos:

Síntesis y caracterización de cristales racémicos de asparagina monohidrato.
Experimentos de calentamiento controlado para observar el comportamiento del cristal.
Análisis de la estructura cristalina y las redes de enlaces de hidrógeno.

Principales resultados:

Los cristales simples de monohidrato de asparagina muestran un salto direccional cuando se calientan.
Los enantiomorfos de los cristales saltan en direcciones opuestas.
El salto direccional se atribuye a los canales orientados que facilitan el escape de las moléculas de agua durante la deshidratación.

Conclusiones:

La quiralidad molecular es un factor clave que rige la dirección del movimiento macroscópico del cristal.
El salto de cristal quiral ofrece un nuevo método para la resolución quiral.
Los hallazgos proporcionan una base para el desarrollo de sistemas de accionamiento que utilizan cristales dinámicos y la comprensión de las correlaciones quiralidad-movimiento.