4.1.8. Geminalni i vicinalni alkoholi
← NatragPonekad se u nazivima diola koriste oznake gem i vic. Geminalni ili gem alkohol ima dvije hidroksilne skupine vezane na isti ugljikov atom. Riječ potječe od latinske riječi gemini što znači blizanci.
Trodimenzijski model geminalnog alkohola butan-2,2-diola
11469045
-OEChem-12081911333D
16 15 0 0 0 0 0 0 0999 V2000
1.5060 0.8572 0.4321 O 0 0 0 0 0 0 0 0 0 0 0 0
0.5108 -0.1565 -1.4226 O 0 0 0 0 0 0 0 0 0 0 0 0
0.4247 0.0365 -0.0130 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9105 0.6953 0.3728 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6164 -1.3278 0.6424 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1473 -0.1048 -0.0116 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9775 1.6763 -0.1158 H 0 0 0 0 0 0 0 0 0 0 0 0
-0.9260 0.8970 1.4512 H 0 0 0 0 0 0 0 0 0 0 0 0
1.6154 -1.7209 0.4181 H 0 0 0 0 0 0 0 0 0 0 0 0
-0.1024 -2.0653 0.2718 H 0 0 0 0 0 0 0 0 0 0 0 0
0.5362 -1.2603 1.7325 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.1635 -0.3250 -1.0833 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.2005 -1.0488 0.5385 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.0504 0.4665 0.2270 H 0 0 0 0 0 0 0 0 0 0 0 0
1.2503 1.7867 0.3095 H 0 0 0 0 0 0 0 0 0 0 0 0
0.0864 0.6024 -1.8567 H 0 0 0 0 0 0 0 0 0 0 0 0
1 3 1 0 0 0 0
1 15 1 0 0 0 0
2 3 1 0 0 0 0
2 16 1 0 0 0 0
3 4 1 0 0 0 0
3 5 1 0 0 0 0
4 6 1 0 0 0 0
4 7 1 0 0 0 0
4 8 1 0 0 0 0
5 9 1 0 0 0 0
5 10 1 0 0 0 0
5 11 1 0 0 0 0
6 12 1 0 0 0 0
6 13 1 0 0 0 0
6 14 1 0 0 0 0
M END
> <PUBCHEM_COMPOUND_CID>
11469045
> <PUBCHEM_CONFORMER_RMSD>
0.4
> <PUBCHEM_CONFORMER_DIVERSEORDER>
1
2
3
> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
5
1 -0.68
15 0.4
16 0.4
2 -0.68
3 0.56
> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
1
> <PUBCHEM_PHARMACOPHORE_FEATURES>
5
1 1 acceptor
1 1 donor
1 2 acceptor
1 2 donor
1 6 hydrophobe
> <PUBCHEM_HEAVY_ATOM_COUNT>
6
> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
0
> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
0
> <PUBCHEM_BOND_DEF_STEREO_COUNT>
0
> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0
> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0
> <PUBCHEM_COMPONENT_COUNT>
1
> <PUBCHEM_CACTVS_TAUTO_COUNT>
1
> <PUBCHEM_CONFORMER_ID>
00AF00F500000001
> <PUBCHEM_MMFF94_ENERGY>
2.6571
> <PUBCHEM_FEATURE_SELFOVERLAP>
25.458
> <PUBCHEM_SHAPE_FINGERPRINT>
139733 1 11454160737484453523
20096714 4 17988637553365273592
21040471 1 18114753727662568835
24536 1 17130707171928245497
29004967 10 16733270036493143785
5943 1 14173263288100624710
> <PUBCHEM_SHAPE_MULTIPOLES>
111.74
2.02
1.1
0.97
1.12
0.36
-0.32
-0.04
0.16
-0.34
0.19
-0.18
-0.09
-0.03
> <PUBCHEM_SHAPE_SELFOVERLAP>
197.055
> <PUBCHEM_SHAPE_VOLUME>
74
> <PUBCHEM_COORDINATE_TYPE>
2
5
10
$$$$
S druge strane, pojam vicinalni ili vic opisuje alkohol kod kojeg su dvije hidroksilne skupine vezane na na dva susjedna ugljikova atoma. Riječ potječe od latinske riječi vicinus što znači susjed.
Trodimenzijski model molekule vicinalnog alkohola butan-2,3-diola
262
-OEChem-12081911353D
16 15 0 1 0 0 0 0 0999 V2000
-0.7966 1.1912 -0.7589 O 0 0 0 0 0 0 0 0 0 0 0 0
0.8041 -1.1950 -0.7530 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.6885 0.3485 0.3866 C 0 0 2 0 0 0 0 0 0 0 0 0
0.6818 -0.3432 0.3844 C 0 0 2 0 0 0 0 0 0 0 0 0
-1.8419 -0.6480 0.3689 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8410 0.6465 0.3719 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7706 0.9848 1.2753 H 0 0 0 0 0 0 0 0 0 0 0 0
0.7682 -0.9788 1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.8528 -1.2302 -0.5588 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.8007 -0.1198 0.4142 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.7858 -1.3355 1.2182 H 0 0 0 0 0 0 0 0 0 0 0 0
2.7958 0.1101 0.4002 H 0 0 0 0 0 0 0 0 0 0 0 0
1.8489 1.2443 -0.5459 H 0 0 0 0 0 0 0 0 0 0 0 0
1.7957 1.3211 1.2320 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.6596 1.6371 -0.7150 H 0 0 0 0 0 0 0 0 0 0 0 0
0.6877 -0.6457 -1.5471 H 0 0 0 0 0 0 0 0 0 0 0 0
1 3 1 0 0 0 0
1 15 1 0 0 0 0
2 4 1 0 0 0 0
2 16 1 0 0 0 0
3 4 1 0 0 0 0
3 5 1 0 0 0 0
3 7 1 0 0 0 0
4 6 1 0 0 0 0
4 8 1 0 0 0 0
5 9 1 0 0 0 0
5 10 1 0 0 0 0
5 11 1 0 0 0 0
6 12 1 0 0 0 0
6 13 1 0 0 0 0
6 14 1 0 0 0 0
M END
> <PUBCHEM_COMPOUND_CID>
262
> <PUBCHEM_CONFORMER_RMSD>
0.4
> <PUBCHEM_CONFORMER_DIVERSEORDER>
4
3
8
7
6
1
5
2
> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
6
1 -0.68
15 0.4
16 0.4
2 -0.68
3 0.28
4 0.28
> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
1
> <PUBCHEM_PHARMACOPHORE_FEATURES>
4
1 1 acceptor
1 1 donor
1 2 acceptor
1 2 donor
> <PUBCHEM_HEAVY_ATOM_COUNT>
6
> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
0
> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
2
> <PUBCHEM_BOND_DEF_STEREO_COUNT>
0
> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0
> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0
> <PUBCHEM_COMPONENT_COUNT>
1
> <PUBCHEM_CACTVS_TAUTO_COUNT>
1
> <PUBCHEM_CONFORMER_ID>
0000010600000004
> <PUBCHEM_MMFF94_ENERGY>
7.1363
> <PUBCHEM_FEATURE_SELFOVERLAP>
20.302
> <PUBCHEM_SHAPE_FINGERPRINT>
139733 1 11167953441432159795
16714656 1 18195813087932384452
20096714 4 18131067181810508016
24536 1 17986383404193681104
29004967 10 18187654664404352419
5943 1 11015648351738658828
> <PUBCHEM_SHAPE_MULTIPOLES>
111.74
2.18
1.15
0.83
0
0
-0.05
0
0.36
0
-0.28
0
0
0.25
> <PUBCHEM_SHAPE_SELFOVERLAP>
195.933
> <PUBCHEM_SHAPE_VOLUME>
74.6
> <PUBCHEM_COORDINATE_TYPE>
2
5
10
$$$$
Prisjetite se reakcija ugljikovodika kojima su nastajali alkoholi. Istražite jesu li u tim reakcijama mogli nastati dioli. Predložite moguće mehanizme sinteze geminalnog i vicinalnog alkohola.
U organskoj kemiji pojam geminalni ili gem opisuje spoj kod kojeg su dva ista heteroatoma ili funkcijske skupine vezane na isti ugljikov atom. S druge strane pojam vicinalni ili vic opisuje spoj kod kojeg su dva ista heteroatoma ili funkcijske skupine vezane na na dva susjedna ugljikova atoma.
Promislite i riješite sljedeći zadatak tako da razvrstate ponuđene pojmove u odgovarajuće blokove.
Geminalni spoj
Vicinalni spoj