화실기_Quantum Chemistry Calculation SN2 Reaction

화실기_Quantum Chemistry Calculation SN2 Reaction_보고서

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1. 1,2-Dichloro-1,2-Difluoroethane stereoisomers

1,2-Dichloro-1,2-Difluoroethane의 (R,R) 형태와 (meso) 형태의 total energy와 dipole moment 값을 비교하였다. (meso) 형태가 (R,R)에 비해 더 낮은 에너지 값을 가지므로 더 안정한 형태임을 확인하였다. 이는 Newmon projection을 통해 (meso) 형태가 anti 형태를 이루어 steric hindrance가 적기 때문인 것으로 분석되었다. 또한 (meso) 형태의 dipole moment가 0에 가까운 값을 가지는 것으로 보아 비극성 분자임을 알 수 있었다.
2. Ethylene and Formaldehyde molecular orbitals

Ethylene과 Formaldehyde의 dipole moment, HOMO와 LUMO 오비탈을 비교하였다. Formaldehyde의 HOMO와 LUMO 에너지 값이 Ethylene보다 낮은 것은 산소 원자 오비탈의 에너지 준위가 더 낮기 때문이다. Ethylene의 HOMO 오비탈은 sp2 혼성화된 2pz 오비탈의 겹침으로 π 결합을 나타내고, LUMO 오비탈은 상쇄간섭으로 node를 가진 π* 오비탈이 형성되었다. Formaldehyde의 HOMO 오비탈은 2px와 1s 오비탈의 보강간섭과 2pz의 상쇄간섭으로, LUMO 오비탈은 2p 오비탈의 상쇄간섭으로 형성되었다.
3. SN2 reaction transition state

F-와 CH3Cl의 SN2 반응에서 transition state의 optimized structure를 확인하였다. F-가 CH3Cl에 후방 접근하면서 C-Cl 결합이 끊어지고 C-F 결합이 형성되는 과정을 관찰하였다. 전이 상태에서는 C가 5배위 구조를 가지며 가장 높은 에너지 상태를 나타내었다. IRC 계산을 통해 반응물, 전이 상태, 생성물의 에너지 변화를 분석한 결과 생성물이 더 안정한 것으로 나타났다.

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1. 1,2-Dichloro-1,2-Difluoroethane stereoisomers

1,2-Dichloro-1,2-difluoroethane is an organic compound with the chemical formula C2H2Cl2F2. It has four possible stereoisomers due to the presence of two chlorine atoms and two fluorine atoms attached to the two carbon atoms. The four stereoisomers are the cis-cis, cis-trans, trans-cis, and trans-trans configurations. The stability and properties of these stereoisomers depend on factors such as steric hindrance, electronegativity differences, and intermolecular interactions. Understanding the stereochemistry of this compound is important in various applications, including refrigerants, solvents, and intermediates in organic synthesis. Analyzing the structural and energetic differences between the stereoisomers can provide insights into their reactivity, selectivity, and potential uses in chemical processes.
2. Ethylene and Formaldehyde molecular orbitals

Ethylene (C2H4) and formaldehyde (CH2O) are two important organic compounds with distinct molecular structures and electronic properties. The molecular orbitals of these molecules play a crucial role in understanding their chemical reactivity and bonding patterns. Ethylene is a simple alkene with a carbon-carbon double bond, and its molecular orbitals consist of sigma (σ) and pi (π) bonds. The sigma bonds are formed by the overlap of sp2-hybridized carbon orbitals, while the pi bonds result from the overlap of p orbitals perpendicular to the molecular plane. Formaldehyde, on the other hand, is a carbonyl compound with a carbon-oxygen double bond. Its molecular orbitals include sigma bonds formed by the overlap of sp2-hybridized carbon and oxygen orbitals, as well as a pi bond between the carbon and oxygen atoms. Understanding the differences in the molecular orbital structures of these compounds can provide insights into their reactivity, stability, and potential applications in organic chemistry and materials science.
3. SN2 reaction transition state

The SN2 (Substitution Nucleophilic Bimolecular) reaction is a fundamental organic chemistry mechanism in which a nucleophile attacks the carbon atom bearing a leaving group, resulting in the substitution of the leaving group. The transition state of an SN2 reaction is a crucial intermediate that plays a significant role in determining the reaction's kinetics and stereochemical outcome. In the SN2 transition state, the nucleophile approaches the carbon atom from the backside, forming a trigonal bipyramidal intermediate. The leaving group occupies an axial position, while the nucleophile and the substituents occupy the equatorial positions. This transition state geometry is characterized by partial bond formation between the nucleophile and the carbon atom, as well as partial bond breaking between the carbon atom and the leaving group. Analyzing the electronic and structural features of the SN2 transition state, such as bond lengths, bond angles, and charge distributions, can provide valuable insights into the reaction mechanism, reactivity, and stereochemical preferences. Understanding the SN2 transition state is essential for predicting and controlling the outcome of various organic reactions, including nucleophilic substitutions, elimination reactions, and enzymatic catalysis.