laporan kimia komputasi

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 : contact@uinsgd.ac.id

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