Using Maestro and Gaussian 09 in the Qualitative analysis of Endiynes (enyne-allenes)

Abstract

By Dr. Robert D. Craig,Ph.D.

-8,10,11 trihydroxy- 9- oxoBicyclo(7:2:2)undec 2- yne,4-ene,6-yne

Harmonic frequencies

(cm**-1), IR intensities (KM/Mole), Raman scattering

activities (A**4/AMU), depolarization ratios for plane and unpolarized

incident light, reduced masses (AMU), force constants (mDyne/A),

and normal coordinates:

C-H in-plane 1000-1300 cm-

C-H out-of-plane and 800-950 cm-

twelve C-H in-plane bending vibrations of 1055.8 – 1503.3 cm

six C-H out-of-plane 800-950 cm

The C-H in-plane and out-of-plane bending vibrations generally lie in the range of 1000-1300 cm- and 800-950 cm- (27-29) , respectively.

In the present case, twelve C-H in-plane bending vibrations are observed at the range of 1055.8 – 1503.3 cm-. the six C-H out-of-plane bending vibrations are observed at the range of 750.2-1011.3 cm- and 678. However, as in any complex molecule, vibrational interactions occur and so, these labels only indicate predominant vibrations

Frequencies -- 46.4430 90.2773 103.9909

IR Inten -- 1.0666 1.2068 2.1074

Frequencies -- 155.9329 178.4513 202.9863

IR Inten -- 2.1698 10.7903 3.3298

Frequencies -- 336.9870 352.3439 376.9907

IR Inten -- 11.0296 13.7006 4.1473

Frequencies -- 336.9870 352.3439 376.9907

IR Inten -- 11.0296 13.7006 4.1473

Frequencies -- 392.4760 418.0662 456.3225

IR Inten -- 12.3402 2.5737 7.0674

Frequencies -- 471.4012 492.1760 506.6196

IR Inten -- 4.8989 100.3815 189.1074

Frequencies -- 595.0455 633.2742 680.9222

IR Inten -- 32.1228 7.9044 21.9926

Frequencies -- 595.0455 633.2742 680.9222

C-H out-of-plane bending vibrations are observed at the range of 750.2-1011.3 cm- and 678.

IR Inten -- 32.1228 7.9044 21.9926

Frequencies -- 695.1723 765.1576 795.5685

C-H out-of-plane bending vibrations are observed at the range of 750.2-1011.3 cm- and 678.

IR Inten -- 30.6751 19.6704 19.8076

Frequencies -- 806.3163 849.8070 917.6558

six C-H out-of-plane 800-950 cm

C-H out-of-plane bending vibrations are observed at the range of 750.2-1011.3 cm- and 678.

IR Inten -- 22.1696 13.7702 16.0880

Frequencies -- 939.3541 1060.9691 1105.0525

six C-H out-of-plane 800-950 cm

C-H in-plane 1000-1300 cm-

IR Inten -- 29.2604 39.8860 45.9391

Frequencies -- 1146.4633 1169.9673 1235.9834

C-H in-plane 1000-1300 cm-

IR Inten -- 125.6572 106.6948 122.8856

Frequencies -- 1281.3576 1304.2065 1330.3879

C-H in-plane 1000-1300 cm-

IR Inten -- 163.0389 5.1197 11.8842

Frequencies -- 1368.2170 1422.4390 1430.1970

IR Inten -- 137.5125 76.1422 16.5024

Atom AN X Y Z X Y Z X Y

Frequencies -- 1436.8364 1484.9419 1489.6613

IR Inten -- 5.2138 16.4951 12.3021

The strong band at 1620 cm- (IR) and 1626 cm- (Raman) has a predominantly mixed v(C=C) character. The frequency of this band is predicted well. The IR intensity is also calculed very well

Frequencies -- 1511.8523 1539.0105 1575.7404

IR Inten -- 0.7920 80.0522 15.1968

Frequencies -- 1592.5735 1727.6637 1779.8043

IR Inten -- 16.0328 14.2064 13.4021

The C-H stretching occurs above 3000 cm- and is typically exhibited as aliphatic C-H stretch (25). In 1994, Roeges (26) showed that, the C-H stretching vibrations of the phenyl (MY CASE IS THE FIVE MEMEBERED RING) are expected in the region 3000-3120 cm. The calculated values of these modes for the target molecule have been found to be 3220.5, 3223.0, 3207.7, 3207.6, 3159.6 and 3183.7 cm- at B3LYP/6-31+G(d,p) level of calculation.

Frequencies -- 3253.3104 3271.6279 3351.2596

IR Inten -- 6.4605 55.3530 8.2315

Frequencies -- 3953.3827 3996.3253 4046.6678

IR Inten -- 117.0801 119.8242 123.7181