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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Prochirality

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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...
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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Conformational Landscape and Polymorphism in 5-Acetic Acid Hydantoin.

B A Nogueira1, G O Ildiz1,2, J Canotilho3

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Quantum chemical calculations and experimental studies explored 5-acetic acid hydantoin (5AAH). Interestingly, the stable room-temperature polymorph adopts the highest-energy conformer geometry of the isolated molecule.

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Area of Science:

  • Computational chemistry
  • Solid-state chemistry
  • Spectroscopy

Background:

  • 5-acetic acid hydantoin (5AAH) is a molecule with potential applications.
  • Understanding its conformational landscape and solid-state behavior is crucial for its use.

Purpose of the Study:

  • To investigate the conformational space of 5AAH using quantum chemical calculations.
  • To experimentally determine the solid-state properties and identify polymorphs of 5AAH.
  • To correlate the molecular geometry in the solid state with theoretical predictions.

Main Methods:

  • Density Functional Theory (DFT) calculations at the B3LYP/6-311++G(d,p) level.
  • Gas-phase to matrix isolation (10 K argon) of the most stable conformer.
  • Infrared spectroscopy and normal coordinate analysis.
  • Differential scanning calorimetry (DSC), polarized light thermal microscopy (PLTM), and Raman spectroscopy.
  • Natural Bond Orbital (NBO) analysis for electronic structure.

Main Results:

  • 13 conformers of 5AAH were identified, with 6 cis and 7 trans arrangements of the carboxylic group.
  • The most stable conformer (cis-I) was isolated and its IR spectrum assigned.
  • Five distinct polymorphs of 5AAH were identified through thermal analysis.
  • The room-temperature stable polymorph surprisingly adopts the geometry of the highest-energy calculated conformer.

Conclusions:

  • The conformational preferences of 5AAH in isolation differ significantly from its stable solid-state form.
  • Experimental techniques confirm the existence of multiple polymorphs, highlighting the complexity of its solid-state behavior.
  • This study provides valuable insights into structure-property relationships for 5AAH, relevant for material design.