chap01-Intro - Chem 4571 Organometallic Chemistry Lecture...

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Organic Chemistry: A Short Course
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Chapter 7 / Exercise 7.10
Organic Chemistry: A Short Course
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Chem 4571 Organometallic Chemistry Lecture Notes Prof. George G. Stanley Department of Chemistry Louisiana State University 614 Choppin Hall (225)-578-3471 E-Mail: [email protected] Spring, 2017 (updated 5/26/2016) 2008 update: electron density discussion, square-planar electronic effects, orbital info added to chapter 1; bonding comparison between PCl3and PMe3added to phosphine chapter. 2012 update: additional problems, minor corrections. 2014 updates: minor corrections. 2015 updates: minor corrections, new examples of formal charge vs. calculated charges via DFT calculations (early chapters). 2016 update: minor corrections & making note chapters & PowerPoint slides correspond better.
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Organic Chemistry: A Short Course
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Chapter 7 / Exercise 7.10
Organic Chemistry: A Short Course
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Intro 2 Fundamentals You Need to Know: 1. Electronegative/Electropositive concepts Where do the partial positive and negative charges in a molecule reside? This is important for determining how much electron (e-) density will be donated from a ligand to a metal and where a nucleophile or electrophile will likely attack for chemical reactions. 2. Electrostatics vs. Electronegativity 3. Lewis dot structures and valence electron counts Important for determining the number of electrons on a ligand and what the charge of the ligand is. We almost always deal with ligands with even #’sof electrons. If a ligand has an odd # of electrons we add additional electrons to get to an even #, usually to form a closed shell electron configuration with a formal negative charge(s). Common Exceptions = Boron & Aluminum. 3. Oxidation States 4. Organic line notation for drawing structures R2PPR2NiClClClClR2PPR2NiClClClClClClR2PPR2NiClClClClClCl
Intro 3 Electron Density Terminology 101: Electron Density:The presence of energetically accessible valence electrons around an atom. Electrons are represented by a probability distribution spread out over a region of space defined by the nature of the orbital: s, p, d, f, and/or hybrid orbitals such sp3, sp2, sp, etc. Atoms with quite a few valence electrons such as Pt(0) d10and/or contracted orbitals have a high electron density. Atoms with fewer valence electrons (e.g., Na+) and/or diffuse orbitals (electrons spread out over a larger region of space) can be considered to have low electron densities. Do not confuse electron density with electronegativity or how electron-rich or poor an atom is classified. Electron-rich:Atoms that are willing to readily donate electrons or electron pairs to other atoms are considered electron rich. Ease of ionization is another property associated with electron-rich atoms. The willingness to share or donate electron pairs is related to lower electronegativity, number of valence electrons, good donor groups on the atom in question, negative charges, or some combination of these factors. Using organic terminology I would consider an electron-rich atom to be a good nucleophile (electron pair donating).

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