laporan kimia komputasi
TRANSCRIPT
LAPORAN KIMIA KOMPUTASI
NITRASI BENZENA“diajukan untuk memenuhi tugas mata kuliah kimia komputasi”
Oleh :
Kelompok 1
A Ba’ist Khaerul Umam
Ani Andriani
Futhri A. K.
JURUSAN KIMIA
FAKULTAS SAINS DAN TEKNOLOGI
UNIVERSITAS ISLAM NEGERI SUNAN GUNUNG DJATI BANDUNG
2014
Jl. A. H. Nasution No.105 Bandung 40614 Telp : (022) 7800525 Fax : (022) 7803936Website : http//www.uinsgd.ac.id Email : [email protected]
2014
A. DESKRIPSI SINGKAT
1) Reaksi subtitusi elektrofilik antara benzen dan asam nitrat
Pengertian: reaksi dalam dimana suatu elektrofil disubstitusikan untuk satu atom hidrogen pada cincin aromatik(benzena). Aromatisitas benzena menyajikan suatu kestabilan yang unik pada sistem phi, dan benzena tidak menjalani kebanyakan reaksi yang khas bagi alkena meskipun demikian benzena tidaklah sekali-kali lamban (inert) pada kondisi yang tepat benzena mudah untuk bereaksi substitusi aromatik elektrofilik.
Benzen direaksikan dengan campuran antara asam nitrat pekat dan asam sulfur pekat pada suhu kurang dari 50°C. Selagi suhu bertambah. Kemungkinan mendapatkan -NO2, tersubsitusi ke cincin bertambah.
Dan terbentuklah nitrobenzen.
atau:
Asam sulfur pekat bereaksi sebagai kalalisator.
2) Formasi dari elektrofil
Yang merupakan elektrofil disini adalah ion nitronium atau kation nitril, NO2+. yang
terbentuk dari reaksi antara asam nitrat dan asam sulfur.
3) Mekanisme substitsusi elektrofilik
Tahap pertama
Tahap kedua
B. STRUKTUR
a) benzena
b) Asam nitrat
c) Nitrobenzena
d) air
C. FLOWCHART
start
Senyawa
(a) C6H6
(b) HNO3
(c) C6H5NO2
(d) H2O
………………………………..
Oasis set N3I
yes
output
………………………………………………..
D. OPTIMASI GEOMETRI
Benzena
$DATA
Benzene
C1C 6.0 -6.39093 1.64519 0.16277C 6.0 -4.93713 1.72840 -0.29337C 6.0 -4.12836 0.52464 0.18266
Gambardanoptimasi
Struktur Avogadro
Perhitungan firefly
Data out putperhitungan
Galaditdanchemcraft
Hasil
Kordinatstruktur
Dan input file
Metode DFT
Energy
elekronik
Spektrum IR dll
start
C 6.0 -4.77728 -0.79538 -0.22630C 6.0 -6.23863 -0.87292 0.20838C 6.0 -7.03824 0.33424 -0.27388H 1.0 -6.95552 2.49040 -0.24674H 1.0 -6.43653 1.72902 1.25551H 1.0 -4.48354 2.65072 0.08692H 1.0 -4.90129 1.78236 -1.38829H 1.0 -4.03255 0.56010 1.27464H 1.0 -3.11365 0.57788 -0.22827H 1.0 -4.21898 -1.63027 0.21264H 1.0 -4.71583 -0.90842 -1.31545H 1.0 -6.29082 -0.93023 1.30242H 1.0 -6.68981 -1.79266 -0.18115H 1.0 -8.06073 0.27937 0.11657H 1.0 -7.11182 0.31032 -1.36801 $END
Asam nitrat
$DATA asnitratC1N 7.0 -2.39428 3.41273 0.00000H 1.0 -3.41588 3.53473 0.00000O 8.0 -2.23322 4.83744 -0.00000O 8.0 -0.97517 3.50727 0.00000O 8.0 -2.19753 2.03144 -0.00000H 1.0 -3.11465 5.26849 0.00000H 1.0 -0.72741 4.44880 -0.00000H 1.0 -3.07219 1.59934 0.00000 $END
Nitrobenzena
$DATA nitrobenzenaC1N 7.0 -2.39935 2.04718 1.19917O 8.0 -3.67251 1.75242 0.73337O 8.0 -1.34828 1.50663 0.47266C 6.0 -3.30845 4.23090 1.85370C 6.0 -3.13177 5.56759 2.20817C 6.0 -2.21835 3.41524 1.52322C 6.0 -1.85199 6.11019 2.24935C 6.0 -0.93805 3.98056 1.58681C 6.0 -0.75278 5.31635 1.94029 $END
Air
$DATA airC1O 8.0 -5.08387 2.06666 0.00000H 1.0 -4.11387 2.06666 0.00000H 1.0 -5.40720 2.64256 -0.71042 $END
E. JARAK ANTAR IKATAN
Benzena
Distance matrix (angstroms): 1 2 3 4 5 1 C 0.000000 2 C 1.392730 0.000000 3 C 2.412265 1.392710 0.000000 4 C 2.785418 2.412240 1.392720 0.000000 5 C 2.412240 2.785434 2.412280 1.392730 0.000000 6 C 1.392721 2.412281 2.785468 2.412265 1.392710 6 6 C 0.000000
Asam nitrat
Distance matrix (angstroms): 1 2 3 4 5 1 H 0.000000 2 N 1.037478 0.000000 3 O 1.960301 1.327203 0.000000 4 O 1.960278 1.327240 2.140385 0.000000 5 O 1.960313 1.327214 2.140071 2.140454 0.000000
Nitrobenzena
Distance matrix (angstroms): 1 2 3 4 5 1 N 0.000000 2 O 1.230736 0.000000 3 O 1.230736 2.180089 0.000000 4 C 2.468218 2.719599 3.566540 0.000000 5 C 3.739977 4.111290 4.710452 1.393059 0.000000 6 C 1.472996 2.316854 2.316854 1.393766 2.394587 7 C 4.233102 4.926620 4.926620 2.418887 1.397374 8 C 2.468218 3.566540 2.719599 2.442096 2.803839 9 C 3.739976 4.710452 4.111290 2.803838 2.424515 10 H 2.657997 2.389803 3.879114 1.082605 2.172010 11 H 4.613261 4.771545 5.670314 2.147775 1.085336 12 H 5.318804 5.990232 5.990232 3.400561 2.154211 13 H 2.657996 3.879113 2.389802 3.410346 3.885970 14 H 4.613261 5.670314 4.771545 3.889170 3.408075 6 7 8 9 10 6 C 0.000000 7 C 2.760106 0.000000 8 C 1.393766 2.418887 0.000000 9 C 2.394587 1.397374 1.393059 0.000000 10 H 2.143697 3.413484 3.410346 3.885970 0.000000 11 H 3.381002 2.157806 3.889170 3.408075 2.505631 12 H 3.845808 1.085702 3.400561 2.154211 4.313115 13 H 2.143697 3.413484 1.082606 2.172011 4.282561 14 H 3.381002 2.157806 2.147775 1.085336 4.971288 11 12 13 14 11 H 0.000000 12 H 2.483250 0.000000 13 H 4.971288 4.313115 0.000000 14 H 4.304787 2.483249 2.505632 0.000000
Air
Distance matrix (angstroms): 1 2 3 1 O 0.000000 2 H 0.969120 0.000000 3 H 0.969120 1.527199 0.000000
F. DIAGRAM TINGKAT ENERGI KESELURUHAN
i. BenzenaENERGY COMPONENTS-----------------
WAVEFUNCTION NORMALIZATION = 1.0000000000
ONE ELECTRON ENERGY = -822.7880967136TWO ELECTRON ENERGY = 332.3632376544NUCLEAR REPULSION ENERGY = 256.2168517674------------------TOTAL ENERGY = -234.2080072919
ELECTRON-ELECTRON POTENTIAL ENERGY = 332.3632376544NUCLEUS-ELECTRON POTENTIAL ENERGY = -1056.9152817295NUCLEUS-NUCLEUS POTENTIAL ENERGY = 256.2168517674------------------TOTAL POTENTIAL ENERGY = -468.3351923077TOTAL KINETIC ENERGY = 234.1271850158VIRIAL RATIO (V/T) = 2.0003452067
ii. NitrobenzenaENERGY COMPONENTS-----------------
WAVEFUNCTION NORMALIZATION = 1.0000000000
ONE ELECTRON ENERGY = -1403.0697632035TWO ELECTRON ENERGY = 558.9506790139NUCLEAR REPULSION ENERGY = 410.1449651119------------------TOTAL ENERGY = -433.9741190776
ELECTRON-ELECTRON POTENTIAL ENERGY = 558.9506790139NUCLEUS-ELECTRON POTENTIAL ENERGY = -1836.9622807769NUCLEUS-NUCLEUS POTENTIAL ENERGY = 410.1449651119------------------TOTAL POTENTIAL ENERGY = -867.8666366511TOTAL KINETIC ENERGY = 433.8925175735VIRIAL RATIO (V/T) = 2.0001880685
iii. Asam nitratENERGY COMPONENTS-----------------
WAVEFUNCTION NORMALIZATION = 1.0000000000
ONE ELECTRON ENERGY = -629.4658737367TWO ELECTRON ENERGY = 226.0806718263NUCLEAR REPULSION ENERGY = 124.3545884048------------------TOTAL ENERGY = -279.0306135056
ELECTRON-ELECTRON POTENTIAL ENERGY = 226.0806718263NUCLEUS-ELECTRON POTENTIAL ENERGY = -908.6222998884NUCLEUS-NUCLEUS POTENTIAL ENERGY = 124.3545884048------------------TOTAL POTENTIAL ENERGY = -558.1870396572TOTAL KINETIC ENERGY = 279.1564261516VIRIAL RATIO (V/T) = 1.9995493113
iv. AirENERGY COMPONENTS-----------------
WAVEFUNCTION NORMALIZATION = 1.0000000000
ONE ELECTRON ENERGY = -123.1186545943TWO ELECTRON ENERGY = 37.8803973344NUCLEAR REPULSION ENERGY = 9.2528980904------------------TOTAL ENERGY = -75.9853591696
ELECTRON-ELECTRON POTENTIAL ENERGY = 37.8803973344NUCLEUS-ELECTRON POTENTIAL ENERGY = -199.1333025360NUCLEUS-NUCLEUS POTENTIAL ENERGY = 9.2528980904------------------TOTAL POTENTIAL ENERGY = -152.0000071113TOTAL KINETIC ENERGY = 76.0146479417VIRIAL RATIO (V/T) = 1.9996146957
molekul E(hartree) E(kJ/mol) Jumlah reaktan dan produk
Entalpi
benzena -234.2080072919 -614913.12290072 -1347507.996229 0
asam nitrat -279.0306135056 -732594.875731
nitrobenzena
-433.9741190776 -1139399.0407769 -1338898.601 8607.3995
air -75.9853591696 -199499.56055916
1Eh = 4.35974394×10−18 J = 2625.5 kJ/mol
G. SPEKTRUM a. Spektrum IR Air
Benzena
Nitrobenzena
Asamnitrat
b. Spektrum raman Benzena
Asam nitrat
Nitrobenzena
Air
c. NMR
Benzena
Asam nitrat
Nitrobenzena
Air
Pustaka
http://www.chemguide.co.uk/mechanisms/elsub/nitration.html
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0104-66322008000100017
Lampiran
Data entalpi
Data spektrum
i. Benzene
IR spektrum
Raman
-
-
NMR
ii. Asam nitrat
IR
Raman
NMR
iii. Nitrobenzena
IR
Raman
NMR
iv. Air
IR spektrum
RAMAN spektrum
NMR