tashkent medical academy department of bioorganic and biological chemistry bioorganic chemistry...
DESCRIPTION
The Questions of: Types of systems Stability of conjugated systems Types of pairing Aromaticity, the criteria of aromaticity Spatial effects Acidity of organic compounds Most of the organic compoundsTRANSCRIPT
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TASHKENT MEDICAL ACADEMY Department of Bioorganic and Biological Chemistry
Bioorganic chemistryFIRST COURSE
SUBJECT: Mutual influence of atoms in molecules of organic compounds, and methods of transmission. PAIRING. Aromaticity. Acidic and basic
organic compounds.LECTURE №2
LECTURER: PROFESSOR A.D.DZHURAEV
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The purpose of the lecture
Generate knowledge of electronic effects as the main
mode of transmission of mutual influence of atoms and electronic structure of molecules with conjugated bonds as thermodynamically stable systems that are used in the construction of biologically important
compounds, as well as build knowledge of acidity and basicity of organic compounds as the most important
properties that determine most of the chemical reactions in living organisms .
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The Questions of:
Types of systemsStability of conjugated systemsTypes of pairingAromaticity, the criteria of aromaticitySpatial effectsAcidity of organic compoundsMost of the organic compounds
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Spatial structure of organic compounds (stereoisomers). CONFIGURATION
Configuration - This spatial arrangement of atoms or atomic groups WITHOUT possible conformations.
Ethane Aminoethanol
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Conformation
Conformation - This different geometric shapes into each other and the resulting atomic groups Spin Around One or more - Communication.
Eclipsed Canted Inhibited
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Energy different conformations
0o 60o 120o 180o 240o 300o
energy
kJ / mol
Torsion angle
Eclipsed Inhibited
canted
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Conformation of cyclic compounds
"Chair" form "Bath" form "Twist" form
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Mutual influence of atoms in the molecule and the way it
TRANSMISSION
Inductive effect
INDUCTIVE EFFECT - mutual influence of atoms SUBMITTED On - Communication
CHH
HCH
HC ClH
H 3 2 1 + + + -+++
123
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Mesomeric effectMesomeric effects - electronic influence vice Submitted
On - Communication.
CH2 CH C O
H
N O-O
CH2 CH Cl ;
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•ELECTRON-DONATING SUBSTITUENTS - DEPUTY SHIFTS THE ELECTRON DENSITY FROM THE SELF.
•TO TREAT THEM - NR2, - NHR, - NH2, - OH, - OR, - CH3 , -I, -BR, -CL, -F
• ELECTRON-WITHDRAWING SUBSTITUENTS - DEPUTY SHIFTS THE ELECTRON DENSITY TO THE ME.
•TO TREAT THEM-NO3, -CN, -SO3H, -COOR, -COOH, -CHO
Electron-donor and electron-withdrawing substituents
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1. CUMULATED SYSTEMС = С = С = С = С – С = С = С =С
2. ISOLATED SYSTEMС = С - (СН 2 )N – С = С
3. CONJUGATE SYSTEMС = С - С = С - С = С - С = С
TYPES OF SYSTEMS
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OPEN INTERFACE CIRCUITСН2 = СН - СН = СН2
BUTADIENE - 1,3
CONJUGATE SYSTEMS
HH
HC C H
HC C
H
H
H H
H H
H
Ñ Ñ Ñ Ñ
1 2
3 4
1 23 4
À
Á
Â
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Conjugated systemsWith Closed Circuit CIRCUIT INTERFACE
P Z - AO
- µî âóð¶à
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TYPES OF INTERFACE
, -pairing - when p - orbitals of all-chain atoms are involved in the formation of - electron cloud, and the formation
of - communication
HH
HC C H
HC C
H
H
H H
H H
H
Ñ Ñ Ñ Ñ
1 2
3 4
1 23 4
À
Á
Â
P Z - AO
- µî âóð¶à
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TYPES OF INTERFACEр, - conjugation – when р- orbitals of the heteroatom involved only in education -electron cloud, but not in
education -communication
СН 2 = СН – CI VINYL CHLORIDE
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1. THE SYSTEM SHOULD HAVE CLOSED FLAT - SKELETON
2. ALL ATOMS IN THE CHAIN MUST BE IN SP2-HYBRIDIZATION
3. RULE HUCKEL SYSTEM SHOULD CONTAIN 4 N + 2 ELECTRONS
Criteria for aromaticity
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BRONSTED ACIDS - ARE NEUTRAL MOLECULES OR IONS, ARE ABLE TO GIVE PROTON (PROTON DONOR).
ACIDITY ORGANIC COMPOUNDS
А - Н + : В А- + В – НAcid basis conjugate conjugate base acid
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СН3СООН + Н2О СН=СОО- + Н3О+ACETIC ACID BASE ACETATE ION HYDRONIUM ION . (СОПРЯЖЕННОЕ ОСНОВ) (СОПРЯЖЕННАЯ К-ТА)
FOR THE REACTION EQUILIBRIUM CONSTANT EQUAL:
Equilibrium constant
ΟΗCΟΟНCΗ
ΟΗCΟΟCΗΚ23
33
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ACIDITY CONSTANT EQUAL VALUE:
Р КА = – LG КА
acidity constantProduct K * [H2O] is constant acidity (Ka)
Н
CC
CCKKa3
332*
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О - Н ACID CARBOXYLIC ACIDS, ALCOHOLS, PHENOLS
S – H ACID THIOLS, THIOETHERS
N – H ACID AMIDES, AMINES, IMIDES
C – H ACID HYDROCARBONS AND THEIR DERIVATIVES
Bronsted acid:
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1. ON THE ABILITY OF THE ATOMS ARE BONDED TO HYDROGEN, KEEP YOURSELF IN ELECTRON PAIR AFTER THE DEPARTURE OF THE PROTON (OT ITS ELECTRONEGATIVITY)
2. THE SIZE OF THE ATOM IS BONDED WITH HYDROGEN (ATOMIC POLARIZABILITY)
3. FROM POSSIBLE DELOCALIZATION (REDISTRIBUTION) OF NEGATIVE CHARGE ON THE OTHER ATOMS (ON THE PRESENCE OF CONJUGATED SYSTEMS)
4. ON THE ABILITY OF THE SOLVATED ANION
Stability anion depends on the following factors:
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С2Н5ОН = С2Н5О- + Н+
С2Н5SН = С2Н5S- + Н+
С2Н5SН > С2Н5 ОН
acidic compounds
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СН– ACID< NH – ACID< OH- ACID<SH- ACID
Increasing the power acidity among Bronsted acid
CH OH CCH3 OH C2H5 OH OH(CH3)2 (CH )3 3
HCOOH> 3 CH COOH>(CH 3)3 C - COOH
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REASONS BRONSTED - THIS NEUTRAL MOLECULES OR IONS, WHICH TAKE PROTON (PROTON ACCEPTOR)
REASONS BRONSTED
Distinguish between two types of Bronsted Reasons: π- GROUNDS n-GROUNDS (onium)
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THESE REASONS TO APPLY - ALKENES, ALKADIENES, ARENA.
CENTER OF MAIN, THAT IS THE POINT OF ATTACHMENT OF THE PROTON, IS THE ELECTRONIC π-COMMUNICATIONS.
π-ОСНОВАНИЯ
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DEPENDING ON THE NATURE OF THE HETEROATOM, THAT IS BY CENTER MAINLY
DIFFER:
А) AMMONIUM Б) OXONIUM
В) SULFONIUM
n-GROUNDS (onium )