Cap 1 Concetti Base di Molecole Organiche
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Cap 1 Concetti Base di Molecole Organiche

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<strong>Cap</strong>itolo I°- CONCETTI BASE DI MOLECOLE<br />

ORGANICHE PER MATERIALI ORGANICI<br />

DONOR, ACCEPTOR, OM, HOMO, LUMO<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

1

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

2

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

3

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

4

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

5

BENZENE<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

6

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

7

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

8

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

9

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

10

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

11

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

12

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

13

Densità <strong>di</strong><br />

carica<br />

Or<strong>di</strong>ne <strong>di</strong><br />

legame<br />

Sistema π neutro<br />

Sistema π eccessivo<br />

DONOR MOLECULE<br />

Sistema π deficiente<br />

ACCEPTOR MOLECULE<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

14

Π EXCESSIVE<br />

RING<br />

Π DEFICIENT<br />

RING<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

15

HOMO e LUMO: Costruzione grafica<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

16

REGOLE DI COMBINAZIONE<br />

GRAFICA<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

17

Chimismo non<br />

semplicemente<br />

spiegabile<br />

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

18

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

19

dove<br />

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

20

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

21

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

22

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

23

Dept. Materials Science, Univ.<br />

Milano-Bicocca<br />

Photonics and Biophotonics<br />

Organics Synthesis –<br />

PhoBOS<br />

24

Dept. Materials Science, Univ.<br />

Milano-Bicocca<br />

Photonics and Biophotonics<br />

Organics Synthesis –<br />

PhoBOS<br />

25

Dept. Materials Science, Univ. Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

27

A cosa servono gli FMO Un caso emblematico: la<br />

reazione <strong>di</strong> DIELS ALDER. Fino agli anni 60-65 veniva<br />

catalogata come “no mechanisn reaction”. E infatti non<br />

è nè una elettrofila, nè una nucleofila nè una ra<strong>di</strong>calica.<br />

Nei tar<strong>di</strong> anni 60 Woodwad e Hoffmann hanno<br />

razionalizzato questa reazione nell’ambito delle<br />

REAZIONI PERICICLICHE, una grande famiglia <strong>di</strong><br />

reazioni della quale fanno parte le reazioni <strong>di</strong><br />

cicload<strong>di</strong>zione (come la Diels Alder),le sigmatropiche<br />

(spostamento <strong>di</strong> atomi <strong>di</strong> idrogeno e/residui alchilci e/o<br />

aromatici lungo una catena insatura), le cheletropiche,<br />

ecc. Può essere razionalizzata con gli FMO.<br />

+<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

28

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

29

Effetto sostituente sulla reazione <strong>di</strong> Diels Alder<br />

I fatti:<br />

Perchè<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

30

Come variano gli HOMO e i Lumo con I sostituenti<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

31

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

32

La Diels<br />

Alder<br />

invertita<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

33

Gli Orbitali Molecolari <strong>di</strong> frontiera (FMO) proposti da Fukui<br />

(Nobel nel ’72) hanno il pregio <strong>di</strong> ricomprendere il contributo <strong>di</strong><br />

Woodward e Hoffmann (Conservazione della simmetria degli<br />

orbitali molecolari – 1966-68 – entrambi Nobel)) e la teoria <strong>di</strong><br />

Pearson e Dillon (Aci<strong>di</strong> e Basi ovvero nucleofili e o elettrofili duri<br />

e molli) proposta in<strong>di</strong>pendentemente attorno al ’68. Gli FMO<br />

sono quinin<strong>di</strong> la teoria unitaria del comportamento<br />

chimico organico racchiusa dall’equazione <strong>di</strong><br />

Klopman-Salem.<br />

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

34

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

35

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

36

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

37

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

38

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

39

Dept. Materials Science, Univ. . Milano-Bicocca<br />

Photonics and Biophotonics Organics Synthesis - PhoBOS<br />

40

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