Structure and Molecular Properties

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Presentation transcript:

Structure and Molecular Properties Summer 2012

Overview Syllabus ChemDraw Structures and intermolecular forces

Intermolecular Forces and Physical Properties Virtual ChemBook, Elmhurst College

Solvents and Boiling Points Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

Boiling Point Trend: Mass Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC 74 amu 85 amu 58 amu 65 amu 32 amu 72 amu hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC 86 amu 88 amu 46 amu 41 amu 18 amu toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC 92 amu 79 amu 60 amu 73 amu 78 amu

Intermolecular Forces Hydrogen bonding Acceptor/donor Dipole/dipole Dipole/induced dipole Induced dipole/induced dipole Also called London dispersion forces VDWs Forces

H-Bond Donor, Acceptor, Neither, or Both Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

Polar Protic, Polar Aprotic, Nonpolar Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

London Forces in Nonpolar Solvents Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

General Principles If molecules are about the same mass H-bonding > Dipole-dipole > Induced dipole Induced dipole is weakest interaction, but as surface area increases, cumulative effect can overcome stronger IMF Strategy for predicting relative boiling points

Solubility “Like dissolves like” Based on IMF

Miscibility and Density Miscibility spectrum Density Organics (0.7 g/mL) Aqueous (1.0 g/mL) Halogenated (1.3 g.mL)

Miscibility with Water Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC