Computational Investigations for Undergraduate Organic Chemistry: Modeling a TLC Exercise to Investigate Molecular Structure and Intermolecular Forces

Hessley, Rita K.

doi:10.1021/ed077p203

Cited by 11 publications

(13 citation statements)

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“…Many excellent laboratory activities and demonstrations require students to use hydrogen bonding and intermolecular force concepts to solve problems (17)(18)(19)(20). However, little concrete evidence is provided to document how these activities improve student understanding.…”

Section: Previous Researchmentioning

confidence: 99%

How Do Organic Chemistry Students Understand and Apply Hydrogen Bonding?

et al. 2001

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Students completing a year-long organic chemistry sequence were interviewed to assess how they understood, explained, and applied knowledge of hydrogen bonding to the physical behavior of molecules. Students were asked to define hydrogen bonding and explain situations in which hydrogen bonding could occur. They were asked to predict and explain how hydrogen bonding influences boiling point, the solubility of molecules, and NMR and IR spectra. Results suggest that although students may be able to give appropriate definitions of hydrogen bonding and may recognize when this phenomenon can occur, significant numbers cannot apply their knowledge of hydrogen bonding to physical properties of molecules or to the interpretation of spectral data. Some possess misconceptions concerning boiling points and the ability of molecules to induce hydrogen bonding. Instructional strategies must be adjusted to address these issues.

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Section: Previous Researchmentioning

confidence: 99%

How Do Organic Chemistry Students Understand and Apply Hydrogen Bonding?

et al. 2001

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“…[9,10] The polarity of the solvent is determined by the intermolecular forces in the solution system, which could be either nonspecific forces (ex: directional force, induced force, dispersion force) or specific forces (ex: hydrogen bond binding force, electron pair acceptor and donor interaction). [11][12][13] As they occur in the solvated shell of the solute, which is comparatively different than that in the solvent body, it belongs to molecular microscopic interaction. [14][15][16] While defining the above three physical constants, the assumed solvation electrostatic model does not consider the specific force, and therefore, it is not ideal to relate the molecular polarity with macroscopic physical quantities.…”

Section: Introductionmentioning

confidence: 99%

“…Usually, parameters such as dipole moment (μ), dielectric constant (ϵ) and refractive index ( n ) are used to characterize and quantitatively describe the polarity of the solvent [9,10] . The polarity of the solvent is determined by the intermolecular forces in the solution system, which could be either non‐specific forces (ex: directional force, induced force, dispersion force) or specific forces (ex: hydrogen bond binding force, electron pair acceptor and donor interaction) [11–13] . As they occur in the solvated shell of the solute, which is comparatively different than that in the solvent body, it belongs to molecular microscopic interaction [14–16] .…”

Section: Introductionmentioning

confidence: 99%

A Solvatochromic Fluorescent Probe for Solvent Polarity Detection Using a Smartphone

et al. 2022

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A solvatochromic fluorescent probe (probe 1) with D-π-A molecular configuration was developed. Probe 1 exhibited excellent polarity sensitivity. The E T (30) value of solvents demonstrated a good linear relationship with the Stokes shift of probe 1 except for DMSO. Moreover, the linear correlation coefficient value reached 0.97. The probe demonstrated different colors based on the type of solvents. With the increase in solvent polarity, the color gradually changed from blue to earthy yellow. It has a linear functional relationship between the B value (Blue, the blue primary color of light in RGB) and E T (30) values of the solvent existed. It provided strong support for the rapid determination of solvent polarity. In addition, probe 1 can be used for the determination of alcohol levels in Baijiu by smartphone.

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“…For the chromatography portion of Exercise 2, each student injects a pure liquid and a mixture of liquids into the GC using a needle-dip technique. 5 Retention times on the GC are recorded and compared to the dipole moments calculated on the computer and to boiling point data (16). Although only one molecular property (boiling point) is examined in this exercise (17), the importance of hydrogen bonding as an intermolecular force is made very clear.…”

Section: W For Introductory Chemistrymentioning

confidence: 99%

“…The sequence expands upon students' knowledge of bonding and VSEPR (valence shell electron pair repulsion) structures to build and submit semi-empirical calculations to MacSpartanPlus (1) 1 ; uses the results to examine molecular shape, dipole moments, and intermolecular forces when coupled with a gas chromatography laboratory exercise; and finishes with an exploration of molecular orbitals. Earlier reports of computational exercises throughout the undergraduate curriculum (2)(3)(4) most often focus on upper-level physical and inorganic chemistry courses with "early" inclusion emphasizing the sophomore-level organic course (5)(6)(7). When these reports have involved first-year courses, the use of modeling software has been limited to viewing molecules and properties without incorporating the build-and-calculate stages required by the method (8) with only a few exceptions (9).…”

mentioning

confidence: 99%